Proposed Rule2025-00321

Guidance Regarding Certain Matters Relating to Nonrecognition of Gain or Loss in Corporate Separations, Incorporations, and Reorganizations

Primary source

Metadata and text below are from the Federal Register, a public-domain U.S. government work. Always verify the official published version before relying on it for any legal matter.

Published
January 16, 2025

Issuing agencies

Treasury DepartmentInternal Revenue Service

Abstract

This document contains proposed regulations regarding certain matters relating to corporate separations, incorporations, and reorganizations qualifying, in whole or in part, for nonrecognition of gain or loss. These matters include distributions and retentions of controlled corporation stock, assumptions of liabilities by controlled corporations, exchanges of property between distributing corporations and controlled corporations, and distributions and transfers of consideration to distributing corporation shareholders and creditors. The proposed regulations would affect corporations and their shareholders and security holders. Proposed regulations modifying the reporting requirements for corporate separations are published elsewhere in the Proposed Rules section of this issue of the Federal Register.

Full Text

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<title>Federal Register, Volume 90 Issue 10 (Thursday, January 16, 2025)</title>
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[Federal Register Volume 90, Number 10 (Thursday, January 16, 2025)]
[Proposed Rules]
[Pages 5220-5295]
From the Federal Register Online via the Government Publishing Office [<a href="http://www.gpo.gov">www.gpo.gov</a>]
[FR Doc No: 2025-00321]



[[Page 5219]]

Vol. 90

Thursday,

No. 10

January 16, 2025

Part VII





 Department of the Treasury





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 Internal Revenue Service





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26 CFR Part 1





Guidance Regarding Certain Matters Relating to Nonrecognition of Gain 
or Loss in Corporate Separations, Incorporations, and Reorganizations; 
Proposed Rule

Federal Register / Vol. 90, No. 10 / Thursday, January 16, 2025 / 
Proposed Rules

[[Page 5220]]


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DEPARTMENT OF THE TREASURY

Internal Revenue Service

26 CFR Part 1

[REG-112261-24]
RIN 1545-BR32


Guidance Regarding Certain Matters Relating to Nonrecognition of 
Gain or Loss in Corporate Separations, Incorporations, and 
Reorganizations

AGENCY: Internal Revenue Service (IRS), Treasury.

ACTION: Notice of proposed rulemaking.

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SUMMARY: This document contains proposed regulations regarding certain 
matters relating to corporate separations, incorporations, and 
reorganizations qualifying, in whole or in part, for nonrecognition of 
gain or loss. These matters include distributions and retentions of 
controlled corporation stock, assumptions of liabilities by controlled 
corporations, exchanges of property between distributing corporations 
and controlled corporations, and distributions and transfers of 
consideration to distributing corporation shareholders and creditors. 
The proposed regulations would affect corporations and their 
shareholders and security holders. Proposed regulations modifying the 
reporting requirements for corporate separations are published 
elsewhere in the Proposed Rules section of this issue of the Federal 
Register.

DATES: Written or electronic comments and requests for a public hearing 
must be received by March 17, 2025.

ADDRESSES: Commenters are strongly encouraged to submit public comments 
electronically via the Federal eRulemaking Portal at <a href="https://www.regulations.gov">https://www.regulations.gov</a> (indicate IRS and REG-112261-24) by following the 
online instructions for submitting comments. Requests for a public 
hearing must be submitted as prescribed in the ``Comments and Requests 
for a Public Hearing'' section. Once submitted to the Federal 
eRulemaking Portal, comments cannot be edited or withdrawn. The 
Department of the Treasury (Treasury Department) and the IRS will 
publish for public availability any comments to the IRS's public 
docket. Send paper submissions to CC:PA:01:PR (REG-112261-24), Room 
5203, Internal Revenue Service, P.O. Box 7604, Ben Franklin Station, 
Washington, DC 20044.

FOR FURTHER INFORMATION CONTACT: Concerning the proposed regulations, 
Justin R. Du Mouchel at (202) 317-6975 (not a toll-free number); 
concerning submissions of comments and requests for a hearing, contact 
the Publications and Regulations branch at (202) 317-6901 (not a toll-
free number) or by email to <a href="/cdn-cgi/l/email-protection#15656077797c767d7074677c7b7266557c67663b727a63"><span class="__cf_email__" data-cfemail="daaaafb8b6b3b9b2bfbba8b3b4bda99ab3a8a9f4bdb5ac">[email&#160;protected]</span></a> (preferred).

SUPPLEMENTARY INFORMATION:

Authority

    This document contains proposed regulations under sections 355, 
357, 361, and 368 of the Internal Revenue Code (Code) that would amend 
26 CFR part 1 (Income Tax Regulations) by providing guidance regarding 
certain matters relating to corporate separations, reorganizations, and 
incorporations qualifying, in whole or in part, for nonrecognition of 
gain or loss. The proposed additions and amendments to the Income Tax 
Regulations are issued pursuant to the express delegations of authority 
to the Secretary of the Treasury or her delegate (Secretary) provided 
under sections 337(d), 361(b)(3), and 7805(a) of the Code.
    Section 337(d) states, in part, that ``[t]he Secretary shall 
prescribe such regulations as may be necessary or appropriate to carry 
out the purposes of the amendments made by subtitle D of title VI of 
the Tax Reform Act of 1986,'' including regulations ``to ensure that 
such purposes may not be circumvented through the use of any provision 
of law or regulations (including the consolidated return regulations 
and part III of this subchapter).'' Relating to the treatment of 
transfers to creditors, the second sentence of section 361(b)(3) states 
that ``[t]he Secretary may prescribe such regulations as may be 
necessary to prevent avoidance of tax through abuse of the preceding 
sentence or [section 361](c)(3).'' Finally, section 7805(a) authorizes 
the Secretary to ``prescribe all needful rules and regulations for the 
enforcement of [the Code], including all rules and regulations as may 
be necessary by reason of any alteration of law in relation to internal 
revenue.''

Background

I. Overview of Section 355

A. Section 355 Transactions

1. In General
    If a transaction satisfies the requirements of section 355 (section 
355 transaction) and other relevant provisions of the Code and Income 
Tax Regulations, the transaction may occur without recognition of any 
gain or loss to the distributing corporation (within the meaning of 
section 355(a)(1)(A)) and without recognition of any gain or loss to, 
or the inclusion of any amount in the income of, the shareholders or 
security holders of the distributing corporation. A section 355 
transaction may take one of the following forms: (i) a spin-off, which 
is a pro rata distribution of stock of the controlled corporation 
(within the meaning of section 355(a)(1)(A)) to shareholders of the 
distributing corporation; (ii) a split-off, which is a distribution of 
stock of the controlled corporation to some (but not all) shareholders 
of the distributing corporation in exchange for some or all of their 
stock of the distributing corporation; or (iii) a split-up, which is a 
liquidating distribution in which the distributing corporation 
distributes to its shareholders, either pro rata or non-pro rata, the 
stock of more than one controlled corporation. As discussed in parts 
I.A.3 and I.A.4 of this Background, a section 355 transaction may occur 
either as a ``section 355(c) distribution'' or as part of a ``divisive 
reorganization.''
2. General Utilities Repeal
    In General Utilities & Operating Co. v. Helvering, 296 U.S. 200 
(1935), the Supreme Court of the United States (Supreme Court) held 
that corporations generally could distribute appreciated property to 
their shareholders without the recognition of any corporate-level gain 
(General Utilities doctrine). Congress repealed the General Utilities 
doctrine beginning with legislation in 1969 and culminating with the 
Tax Reform Act of 1986 (Public Law 99-514, 100 Stat. 2085), which, 
among other changes, amended sections 311, 336, and 337 of the Code 
(originally enacted in the Internal Revenue Code of 1954 (1954 Code) 
(Public Law 83-591, 68A Stat. 3) to apply gain and loss recognition to 
non-liquidating and liquidating distributions, respectively.
    Notwithstanding the repeal of the General Utilities doctrine, 
section 355 allows a distributing corporation to distribute the stock 
and securities of a subsidiary (that is, a controlled corporation) to 
its shareholders without imposing a corporate-level tax on the 
distribution. Accordingly, as observed by the United States Tax Court 
(Tax Court), ``more attention has been directed toward [s]ection 355 
today than was ever the case in the past [because] it is one of the few 
(some might say the only) viable opportunity to escape the repeal of 
the General Utilities doctrine.'' McLaulin v. Comm'r, 115 T.C. 255, 266 
(2000).
    In connection with the repeal of the General Utilities doctrine, 
Congress authorized the Treasury Department to promulgate regulations 
to carry out the purposes of that repeal, including by

[[Page 5221]]

preventing its avoidance. Specifically, section 337(d) directs the 
Secretary to prescribe regulations that are necessary or appropriate to 
carry out the purposes of General Utilities repeal, including 
``regulations to ensure that such purposes may not be circumvented 
through the use of any provision of law or regulations (including . . . 
part III of this subchapter).'' Section 355, among other corporate 
organization and reorganization provisions, is included in part III of 
subchapter C of chapter 1 of the Code (subchapter C).
3. Section 355(c) Distributions
    The general rule set forth in section 355(c)(1) provides that no 
gain or loss is recognized to a distributing corporation upon any 
distribution to which section 355 (or so much of section 356 of the 
Code as relates to section 355) applies and that is not made pursuant 
to a plan of reorganization (section 355(c) distribution). However, if 
the distributing corporation distributes any property other than stock 
or securities of a controlled corporation (that is, any property other 
than qualified property, as defined in section 355(c)(2)(B)) in a 
section 355(c) distribution, and if the fair market value of that 
property exceeds the distributing corporation's adjusted basis in that 
property, then section 355(c)(2)(A) requires the distributing 
corporation to recognize gain as if the property were sold to the 
distributee at its fair market value. This Federal income tax treatment 
reflects the status of section 355 as a narrow exception to General 
Utilities repeal. Compare section 311(b).
    Because a section 355(c) distribution is not made pursuant to a 
plan of reorganization, a section 355(c) distribution (unlike a 
divisive reorganization) does not permit the distributing corporation 
to satisfy distributing corporation debt constituting securities with 
property other than qualified property. In other words, because a 
section 355(c) distribution does not qualify as a reorganization under 
the definitional provisions of section 368(a)(1), the operative 
provision set forth in section 361(b)(3) is not applicable. Therefore, 
in a section 355(c) distribution, a distributing corporation cannot 
transfer any property other than qualified property to its creditors 
(including its security holders) without recognizing gain or loss on 
that transfer.
4. Divisive Reorganizations
    A distributing corporation may carry out a section 355 transaction 
as part of a transaction that qualifies as a reorganization under 
section 368(a)(1)(D) or (G) and to which section 354 of the Code (or so 
much of section 356 as relates to section 354) does not apply (divisive 
reorganization). Section 368(a)(1)(D) provides, in part, that a 
reorganization includes a transfer by the distributing corporation of 
all or a part of its assets to a controlled corporation if, immediately 
after the transfer, the distributing corporation or one or more of its 
shareholders (including persons who were shareholders immediately 
before the transfer) are in control (within the meaning of section 
368(c)) of the controlled corporation; but only if, pursuant to the 
plan of reorganization, stock or securities of the controlled 
corporation are distributed in a transaction that qualifies under 
section 355 or 356.
    Under section 368(a)(1)(G), a transfer by a distributing 
corporation of all or a part of its assets to a controlled corporation 
in a case under title 11 of the United States Code or a similar case 
described in section 368(a)(3)(A)(ii) (title 11 or similar case) also 
is a divisive reorganization if, pursuant to the plan of 
reorganization, stock or securities of the controlled corporation are 
distributed in a transaction that qualifies under section 355 (or so 
much of section 356 as relates to section 355). Section 368(a)(3)(C) 
provides an ordering rule under which a transaction that would qualify 
both under section 368(a)(1)(G) and, among other provisions, under 
section 368(a)(1)(D) or section 351 of the Code, is treated as 
qualifying solely under section 368(a)(1)(G) for all purposes of 
subchapter C other than section 357(c)(1).
    If a transaction satisfies the definitional requirements of section 
368(a)(1)(D) or (G), the distributing corporation may qualify for 
nonrecognition treatment for (i) its exchange of property with the 
controlled corporation, (ii) its distribution of certain property to 
its shareholders, and (iii) its transfer of certain property to its 
creditors. Under section 357(a), the controlled corporation generally 
may assume distributing corporation liabilities without the 
distributing corporation recognizing gain or loss, except as provided 
in (i) section 357(b) (if the principal purpose for the liability 
assumption is to avoid Federal income tax or is not a bona fide 
business purpose), and (ii) section 357(c) (if the sum of the amount of 
liabilities assumed by the controlled corporation is greater than the 
total adjusted basis of assets transferred in the exchange).
    Under section 361(a), the distributing corporation recognizes no 
gain or loss if it exchanges property pursuant to the plan of 
reorganization solely for stock and securities in the controlled 
corporation. Under section 361(b)(1)(A), if section 361(a) would apply 
to an exchange but for the fact that the property received by the 
distributing corporation also includes money or other property, no gain 
will be recognized by the distributing corporation if it distributes 
the money or other property pursuant to the plan of reorganization. 
Under section 361(b)(3), the distributing corporation also generally 
may transfer that money or other property in connection with the 
reorganization to its creditors in satisfaction of distributing 
corporation debt held by those creditors, without recognition of gain 
or loss under section 361(b)(1)(A) to the extent the sum of the money 
and the fair market value of the other property transferred to such 
creditors does not exceed the adjusted bases of such assets transferred 
(reduced by the amount of liabilities assumed within the meaning of 
section 357(c)).
    Under section 361(c)(1), the distributing corporation recognizes 
neither gain nor loss on its distribution of qualified property to its 
shareholders pursuant to the plan of reorganization. For this purpose, 
section 361(c)(2)(B) defines ``qualified property'' as any stock in, 
right to acquire stock in, or obligation of (i) the distributing 
corporation, or (ii) another corporation that is a party to the 
reorganization (for example, the controlled corporation) if such stock, 
stock right, or obligation is received by the distributing corporation 
in the exchange. In connection with the reorganization, the 
distributing corporation also generally may transfer that qualified 
property to its creditors in satisfaction of distributing corporation 
debt held by those creditors, without recognition of gain or loss under 
section 361(c).
    For purposes of this preamble, the term ``section 361 
consideration'' means, as described in section 361(a) and (b), the 
consideration received by a target corporation from an acquiring 
corporation in exchange for property transferred by the target 
corporation to the acquiring corporation pursuant to a plan of 
reorganization. Accordingly, in the context of a divisive 
reorganization, the term ``section 361 consideration'' means, for 
purposes of this preamble, the consideration received by the 
distributing corporation from the controlled corporation in exchange 
for property transferred by the distributing corporation to the 
controlled corporation pursuant to the plan of reorganization.

[[Page 5222]]

B. General Federal Income Tax Consequences to Distributing Corporation 
Shareholders

    Section 355(a)(1) provides that, if a distributing corporation 
distributes to its shareholders with respect to its stock, or 
distributes to its security holders in exchange for their securities, 
solely stock or securities of a controlled corporation, and if certain 
other requirements are satisfied, then no gain or loss is recognized 
by, and no amount is included in the income of, the distributing 
corporation's shareholders or security holders upon the receipt of 
stock or securities of the controlled corporation. However, if any 
property is received that is not permitted to be received under section 
355(a)(1), then section 356 (and not section 355) applies to the 
receipt of such property as provided in sections 355(a)(4)(A) and 356.

C. General Requirements for Qualification Under Section 355

    To qualify as a section 355 transaction under section 355(a)(1), a 
transaction must satisfy the following requirements. First, under 
section 355(a)(1)(A), the distributing corporation must distribute 
stock or securities of a controlled corporation to a shareholder with 
respect to distributing corporation stock, or to a security holder in 
exchange for its securities. Second, under section 355(a)(1)(B), the 
transaction may not be used principally as a device for the 
distribution of the earnings and profits of the distributing 
corporation, the controlled corporation, or both. Third, under section 
355(a)(1)(C), the distributing corporation and each controlled 
corporation must satisfy the active trade or business requirements of 
section 355(b).
    With particular regard to these proposed regulations, section 
355(a)(1) imposes a fourth requirement regarding distributions of 
controlled corporation stock and securities. Specifically, section 
355(a)(1)(D) requires that, ``as part of the distribution,'' the 
distributing corporation must distribute either (i) all stock and 
securities in the controlled corporation held by the distributing 
corporation immediately before the distribution, or (ii) an amount of 
stock in the controlled corporation constituting ``control'' within the 
meaning of section 368(c) (control distribution). In the case of 
distributions of less than 100 percent of stock in the controlled 
corporation, it must be established to the satisfaction of the 
Secretary that the retention by the distributing corporation of stock 
(or stock and securities) of the controlled corporation was not 
pursuant to a plan having as one of its principal purposes the 
avoidance of Federal income tax. For purposes of this preamble, such a 
retention of controlled corporation stock (or stock and securities) by 
the distributing corporation is referred to as a ``retention,'' and the 
requirements in section 355(a)(1)(D) are referred to collectively as 
the ``distribution requirement.''

D. The Distribution Requirement and Retentions

1. Overview
    As described in part I.C of this Background, the distribution 
requirement consists of two alternative rules. Under section 
355(a)(1)(D)(i), the distributing corporation will satisfy the 
distribution requirement if it distributes all stock and securities in 
the controlled corporation held by the distributing corporation 
immediately before the distribution. Alternatively, under section 
355(a)(1)(D)(ii), the distributing corporation will satisfy the 
distribution requirement if it satisfies the following two discrete 
requirements: (i) the distributing corporation distributes an amount of 
controlled corporation stock sufficient to qualify as a control 
distribution; and (ii) the distributing corporation establishes to the 
satisfaction of the Secretary that the retention of any controlled 
corporation stock or securities was not pursuant to a plan having as 
one of its principal purposes the avoidance of Federal income tax.
2. Requirements for Control Distribution; Commissioner v. Gordon
    Section 355(a)(1)(D) provides that, if a distributing corporation 
does not distribute all its stock and securities in the controlled 
corporation, the distributing corporation must make a control 
distribution as ``part of the distribution.'' However, section 
355(a)(1)(D) does not expressly impose a temporal requirement for 
making a control distribution. Accordingly, section 355(a)(1)(D) could 
be read as permitting a control distribution to occur over multiple 
taxable years of the distributing corporation.
    In Commissioner v. Gordon, 391 U.S. 83 (1968), the Supreme Court 
considered the application of the distribution requirement to 
distributions by Pacific Telephone and Telegraph Company (Pacific) of 
stock of a newly formed, wholly owned subsidiary (Northwest) over 
multiple taxable years of Pacific. American Telephone and Telegraph 
Company (AT&T), which owned approximately 90 percent of the stock of 
Pacific, decided to separate Pacific into two separate companies and, 
to effectuate that separation, caused Pacific to engage in the 
following transactions. First, pursuant to a plan of reorganization 
submitted to its shareholders, Pacific issued to its shareholders 
(including the taxpayer) transferable rights to acquire approximately 
57 percent of the stock of Northwest on September 29, 1961. That plan 
of reorganization also provided that Pacific had an ``expectation'' 
that the remaining 43 percent of Northwest stock would be offered to 
Pacific's shareholders. Among other reasons for not distributing 100 
percent of its Northwest stock, Pacific desired to achieve an 
appropriate capital structure and avoid potential State regulatory 
issues. On June 12, 1963, Pacific issued to its shareholders 
transferable rights to acquire the remaining 43 percent of Northwest 
stock. The taxpayer contended that the 1961 and 1963 distributions 
collectively qualified under section 355.
    The Court concluded that neither distribution qualified under 
section 355, notwithstanding Pacific's ``expectation'' regarding the 
second distribution and its purposes for making multiple distributions. 
Gordon, 391 U.S. at 98. In its analysis, the Court expressed a general 
principle of Federal income tax that, ``[a]bsent other specific 
directions from Congress, Code provisions must be interpreted so as to 
conform to the basic premise of annual tax accounting.'' Id. at 96. 
With regard to the distribution requirement, the Court noted that, if 
an initial transfer of less than a controlling interest in the 
controlled corporation is to be treated for Federal income tax purposes 
as a mere first step in the divestiture of control, ``it must at least 
be identifiable as such at the time it is made.'' Id. The Court further 
stated that the requirement that the character of a transaction be 
determinable ``does not mean that the entire divestiture must 
necessarily occur within a single tax year,'' but it does mean that, if 
one transaction is to be characterized as a ``first step,'' then 
``there must be a binding commitment to take the later steps.'' Id. Of 
particular relevance to both the IRS's administrative function and the 
objective of these proposed regulations to provide increased certainty 
(see part IV of this Background), the Court expressed that it would be 
wholly inconsistent with the annual accounting premise to hold that the 
essential character of a transaction, and its Federal income tax 
impact, should remain ``not only undeterminable but unfixed for an

[[Page 5223]]

indefinite and unlimited period in the future, awaiting events that 
might or might not happen.'' Id.
    The Court found that the facts and circumstances of Pacific's 
staggered distributions of Northwest stock, as reflected in Pacific's 
plan of reorganization, failed the binding-commitment standard set 
forth by the Court. Id. at 97. Although Pacific's plan of 
reorganization evidenced an expectation to distribute its remaining 
Northwest stock within a three-year period following its initial 57-
percent distribution, the Court emphasized that ``there is obviously no 
promise to sell any particular amount of stock, at any particular time, 
at any particular price'' set forth in that document. Id. Instead, 
Pacific's plan of reorganization merely stated that such subsequent 
distributions would occur ``[a]t a time or times related to its 
(Pacific's) need for new capital.'' Id. Consequently, the Court 
reasoned that, ``[i]f the 1961 distribution played a part in what later 
proved to be a total divestiture of the Northwest stock, it was not, in 
1961, either a total divestiture or a step in a plan of total 
divestiture.'' Id. at 97-98.
3. Retentions
    Section 1.355-2(e), which reiterates the distribution requirement, 
provides that the corporate business purpose or purposes for the 
distribution ordinarily will require the distribution of all stock and 
securities of the controlled corporation. If the distributing 
corporation retains any controlled corporation stock or securities, and 
if it is not established to the satisfaction of the Commissioner that 
the retention was not pursuant to a plan having as one of its principal 
purposes the avoidance of Federal income tax, section 355 does not 
apply to the entire distribution (that is, the entire distribution 
fails to qualify as a section 355 transaction).
    In Rev. Rul. 75-321, 1975-2 C.B. 123, the IRS addressed whether the 
retention by a widely held and publicly traded corporation 
(Distributing) of stock in its banking subsidiary (Controlled) complied 
with section 355(a)(1)(D)(ii) (that is, whether the retention was 
pursuant to a plan having as one of its principal purposes the 
avoidance of Federal income tax). In this revenue ruling, Distributing 
distributed 95 percent of the stock of Controlled to Distributing's 
shareholders to comply with Federal banking laws in a transaction that 
otherwise satisfied the requirements of section 355. Distributing 
retained 5 percent of Controlled's stock to meet collateral 
requirements for short-term financing. The IRS concluded that the 
retention was not pursuant to a plan having as one of its principal 
purposes the avoidance of Federal income tax, because (i) a genuine 
separation of the corporate entities was effectuated, (ii) retention of 
a 5-percent stock interest in Controlled would not enable Distributing 
to maintain practical control over Controlled following the 
distribution, and (iii) a sufficient corporate business purpose existed 
for Distributing's retention of the 5-percent interest in Controlled. 
See also Rev. Rul. 75-469, 1975-2 C.B. 126 (similar ruling with respect 
to a distributing corporation's retention of controlled corporation 
securities to serve as collateral for a bank loan to the distributing 
corporation).
    Similarly, in G.C.M. 32136 (Oct. 23, 1961), the IRS considered 
whether the retention by a distributing corporation (Distributing) of 
stock in a newly formed controlled corporation (Controlled) was 
pursuant to a plan having as one of its principal purposes the 
avoidance of Federal income tax. Under the facts described in that 
memorandum, Distributing distributed 80 percent of Controlled stock to 
Distributing's shareholders to comply with State banking laws in a 
transaction that otherwise satisfied the requirements of section 355, 
and Distributing retained 20 percent of Controlled stock. The avowed 
purpose for the retention was to permit a controlling group of 
Distributing's shareholders to maintain effective control over 
Controlled. In concluding that Distributing had a Federal income tax 
avoidance purpose for the retention, the IRS determined that the 
requirement that a retention be specially justified ``seems most likely 
to be intended to insure a genuine separation.'' See also G.C.M. 32380 
(Aug. 24, 1962) (reiterating that view).

II. Definitional and Operative Provisions Regarding Reorganizations

A. Overview

    Subchapter C generally includes (i) definitional provisions, 
including under section 368, and (ii) operative provisions, including 
under sections 354, 356, 357, and 361. See, for example, Microdot, Inc. 
v. United States, 728 F.2d 593, 598 (2d Cir. 1984) (``Section 368(a)(1) 
is a definitional section, wholly distinct from [section] 354.''). As 
described in greater detail in part II.B of this Background, section 
368(a)(1) defines the term ``reorganization'' as seven specifically 
described types of transactions under subparagraphs (A) through (G). 
Qualification of a transaction (or series of transactions) for a 
definitional provision under section 368(a)(1) is the sole manner by 
which the application of an operative provision relating to a 
reorganization can occur. This statutory structure ensures that the 
tax-advantaged treatment provided by such operative provisions applies 
exclusively to those transactions that satisfy all statutory, 
regulatory, and judicial requirements for a particular definitional 
provision (for example, the continuity of interest and continuity of 
business enterprise requirements). As discussed in greater detail in 
part III of this Background, a primary purpose of the ``plan of 
reorganization'' requirement is to ensure that a transaction to which 
an operative provision is purported to apply is sufficiently connected 
to a reorganization defined in section 368(a)(1).

B. Section 368: Definitions Relating to Corporate Reorganizations

    Section 368(a)(1) is the primary definitional provision of 
subchapter C with regard to reorganizations. For purposes of parts I 
through III of subchapter C, section 368(a)(1) defines the term 
``reorganization'' to mean any of the seven types of transactions 
described in section 368(a)(1)(A) through (G), including triangular 
reorganizations (as defined in Sec.  1.358-6(b)(2)) that are variants 
of such transactions and divisive reorganizations described in section 
368(a)(1)(D) and (G). Section 368(a)(2) provides special rules that 
support the definitional provisions set forth in section 368(a)(1), and 
section 368(a)(3) similarly provides additional rules relating to title 
11 or similar cases.
    Section 368(b) and (c) also contains definitional provisions. For 
purposes of part III of subchapter C, section 368(b) generally defines 
the term ``a party to a reorganization'' to include (i) a corporation 
resulting from a reorganization, and (ii) both corporations, in the 
case of a reorganization resulting from the acquisition by one 
corporation of stock or properties of another. Section 368(b) defines 
other corporations as parties to a transaction depending on the type of 
transaction. See also Sec.  1.368-2(f).
    For purposes of subchapter C (other than sections 304 and 385 of 
the Code), section 368(c) defines the term ``control'' to mean the 
ownership of (i) stock possessing at least 80 percent of the total 
combined voting power of all classes of stock entitled to vote, and 
(ii) at least 80 percent of the total number of shares of all other 
classes of stock of the corporation. See also Rev. Rul. 59-259, 1959-2 
C.B. 115 (requiring

[[Page 5224]]

ownership of (i) stock possessing at least 80 percent of the total 
combined voting power of all classes of voting stock, and (ii) at least 
80 percent of the total number of shares of each class of outstanding 
non-voting stock).

C. Section 357: Assumptions of Liabilities by Transferee Corporations

1. Overview
    Section 357 is an operative provision that facilitates exchanges 
involving the assumption of liabilities by generally preventing such 
assumptions from (i) being treated as the receipt of money or other 
property in an exchange, and (ii) disqualifying the exchange for 
nonrecognition treatment. See section 357(a); see also the anti-abuse 
rule in section 357(b) and the adjusted basis limitation in section 
357(c). Section 357 reflects Congress's view that, ``[i]n typical 
transactions changing the form or entity of a business it is not 
customary to liquidate the liabilities of the business and such 
liabilities are almost invariably assumed by the corporation which 
continues the business,'' but that nonrecognition treatment in section 
357 should be limited solely to ``bona fide transactions of this 
type.'' H.R. Rep. No. 76-855, at 19 (1939) (Conf. Rep.).
2. Response to United States v. Hendler
    The original predecessor to current section 357, section 112(k) of 
the Internal Revenue Code of 1939 (1939 Code), was enacted by Congress 
as section 213(a) of the Revenue Act of 1939 (Public Law 76-155, 53 
Stat. 862, 870) to address the adverse consequences of judicial and 
taxpayer interpretations of the Supreme Court's decision in United 
States v. Hendler, 303 U.S. 564 (1938). See S. Rep. No. 76-648, at 3 
(1939) (referencing the Hendler opinion by name). In Hendler, the Court 
examined the Federal income tax consequences of a transaction that 
qualified as a reorganization under section 112 of the Revenue Act of 
1928 (Public Law 70-562, 45 Stat. 791). As part of the reorganization, 
the transferee corporation (Borden Company) assumed and paid the 
indebtedness of the transferor (Hendler Company). The Court regarded 
the assumption and payment in substance as though the Borden Company 
had made the payment directly to the Hendler Company. Hendler, 303 U.S. 
at 566. Based on that treatment, the Court viewed the Hendler Company 
in substance as receiving money or other property that it failed to 
distribute to its shareholders (because that payment was made to a 
Hendler Company creditor, albeit in form by the Borden Company). Id. 
Accordingly, the Court held that the Hendler Company recognized gain in 
the amount of that payment. Id. at 567.
    Following the Hendler decision, Congress observed that the Court's 
analysis had ``been broadly interpreted to require that, if a 
taxpayer's liabilities are assumed by another party in what is 
otherwise a tax-free reorganization, gain is recognized to the extent 
of the assumption.'' H.R. Rep. No. 76-855, at 19 (emphasis added). In 
other words, as successfully argued by the IRS in cases following 
Hendler, a transferee corporation's lack of payment of the liabilities 
was immaterial for the Hendler analysis to apply to treat the 
transferee corporation's assumption of a transferor's liabilities as a 
cash payment to the transferor. See Haass v. Comm'r, 37 B.T.A. 948, 955 
(1938). The IRS advocated for this broad interpretation in response to 
an aggressive position taken by taxpayers, who relied on the Hendler 
decision to argue that the basis of stock they had received in prior 
exchanges should be increased by the amount of gain that should have 
been recognized and taxed by reason of the transferee corporation's 
assumption of liabilities, even though that gain had not actually been 
taxed by the IRS (and that tax had not been paid).
    However, this broad interpretation jeopardized the nonrecognition 
treatment of bona fide assumptions carried out as part of 
reorganizations that Congress originally had intended to facilitate 
through the enactment of the reorganization provisions. See H.R. Rep. 
No. 76-855, at 19 (``Your committee therefore believes that such a 
broad interpretation as is indicated above will largely nullify the 
provisions of existing law which postpone the recognition of gain in 
such cases.'').
3. Enactment of Section 357(a) and (b)
    Congress enacted section 112(k) of the 1939 Code to balance (i) the 
need to facilitate the bona fide assumption of liabilities in 
transactions that satisfy the definitional requirements of a 
reorganization, with (ii) the need to minimize abusive tax planning 
through such assumptions (including through transitory transactions). 
Accordingly, section 112(k) of the 1939 Code provided for both (i) the 
general nonrecognition treatment adopted by section 357(a) of the 1954 
Code and set forth in current section 357(a), and (ii) a supporting 
anti-abuse provision adopted by section 357(b) of the 1954 Code and set 
forth in current section 357(b).
    Under section 357(b)(1), the total amount of liabilities assumed in 
an assumption described in section 357(a) is treated for purposes of 
section 351 or 361 (as applicable) as money received by the transferor 
in the exchange if it appears that the principal purpose of the 
transferor with respect to the assumption was (i) to avoid Federal 
income tax on the exchange, or (ii) not a bona fide business purpose. 
In effect, section 357(b) can apply to a transaction to preserve the 
treatment required by Hendler for such abusive assumptions.
    In making the determination required by section 357(b)(1), the 
nature of the liabilities and the circumstances under which the 
arrangement for the assumption was made are taken into account. In 
addition, section 357(b)(2) provides that, in any suit or proceeding in 
which the burden is on the transferor to prove that the liability 
assumption should not be treated as money received in the exchange, the 
transferor must meet that burden by a clear preponderance of the 
evidence.
4. Application of Section 357(b) to Divisive Reorganizations
    In Rev. Rul. 79-258, 1979-2 C.B. 143, the IRS considered the 
application of section 357(b) to the assumption by a newly formed 
transferee corporation (Controlled) of a liability incurred by the 
transferor (Distributing) in close temporal proximity to, and in 
anticipation of, a transaction that qualified as a divisive 
reorganization under sections 355 and 368(a)(1)(D). One of the 
Distributing liabilities that Distributing desired Controlled to assume 
was a $4,000x portion of a $25,000x long-term debt owed to an insurance 
company that Distributing had incurred in connection with the business 
transferred to Controlled, and that had been outstanding for several 
years before the divisive reorganization (historical Distributing 
debt). However, Distributing could not apportion the historical 
Distributing debt between it and Controlled because the insurance 
company refused to relieve Distributing of its primary liability for 
repayment.
    Therefore, in exchange for $4,000x in loan proceeds, Distributing 
issued a new long-term note for which Distributing was primarily liable 
to a bank (new Distributing debt). Distributing then caused Controlled 
to assume the new Distributing debt in the divisive reorganization, and 
Distributing was relieved of its primary repayment liability 
(Controlled assumption). The proceeds of the new Distributing debt were 
used by Distributing to pay off $4,000x of the historical Distributing 
debt. Distributing then distributed the Controlled stock to 
Distributing's shareholders.

[[Page 5225]]

    From Distributing's standpoint, having Controlled assume the new 
Distributing debt was desirable because, absent Controlled's assumption 
of this debt, Distributing's assets would be reduced by the value of 
the Controlled stock (which was distributed to Distributing's 
shareholders), but Distributing's liabilities would not be reduced by 
the $4,000x liability attributable to the business transferred to 
Controlled. As a result, Distributing's ability to borrow (and its 
ability to pay off the portion of the historical Distributing debt 
attributable to the business transferred to Controlled) could be 
adversely affected if Controlled did not assume the new Distributing 
debt.
    To determine the potential application of section 357(b), the IRS 
engaged in a detailed analysis of the facts and circumstances relating 
to the issuance of the new Distributing debt and the Controlled 
assumption. First, the IRS observed that Distributing used the proceeds 
of the new Distributing debt to satisfy $4,000x of the historical 
Distributing debt, thereby placing Distributing and Controlled in the 
same net economic position after the Controlled assumption as each 
corporation would have been in had Controlled been able to assume 
$4,000x of the historical Distributing debt. Second, the IRS observed 
that the incurrence of the new Distributing debt and the Controlled 
assumption not only were necessary to effectuate the divisive 
reorganization, but also were a normal adjunct to the divisive 
reorganization given the non-assumable nature of part of the historical 
Distributing debt. Third, the IRS observed that Distributing's 
incurrence of the new Distributing debt and the Controlled assumption 
merely were in substitution for Controlled's assumption of a pro rata 
portion of the historical Distributing debt that Controlled could not 
assume. In that regard, because the divisive reorganization resulted in 
Controlled assuming a liability in an amount that properly related to 
its business operations and would be satisfied from earnings generated 
by those operations, the IRS viewed the incurrence of the new 
Distributing debt and the Controlled assumption as consistent with 
sound business practice. Accordingly, the IRS concluded that tax 
avoidance was not a principal purpose of the transaction and, 
therefore, that section 357(b) did not apply to the Controlled 
assumption.
    Additionally, the IRS determined that the acquisition of the new 
Distributing debt and the Controlled assumption would not be viewed for 
Federal income tax purposes as if Controlled had obtained the new 
Distributing debt and transferred the proceeds to Distributing. In this 
regard, the IRS found it immaterial that Distributing and Controlled 
may have been able to arrange their affairs in another manner, because 
the taxpayer satisfied its burden of proof as required under section 
357(b). See Simpson v. Comm'r, 43 T.C. 900, 916 (1965) (stating that 
the application of section 357(b) is limited to transactions ``arranged 
primarily so that the assumption of the [transferor]'s liability in the 
transaction itself results in tax avoidance for the transferor, or has 
no bona fide business purpose,'' and that section 357(b) was not 
intended to require recognition of gain on bona fide transactions 
designed to rearrange one's business affairs in such a manner as to 
minimize taxes in the future, consistent with existing provisions of 
the law); ISC Industries, Inc. v. Comm'r, T.C. Memo. 1971-283 
(concluding that petitioner's principal purpose in having a new 
subsidiary assume liabilities placed upon the assets transferred to the 
subsidiary was not to avoid Federal income taxes on the transfer, but 
rather was to protect lines of credit for petitioner's finance 
business, and finding it immaterial that petitioner may have been able 
to arrange its affairs in another manner, or in a manner that produced 
more tax revenue, because section 357(b) clearly looks to the 
taxpayer's motives for doing what actually occurred).
5. Application of Section 357(c)
    In the case of an exchange to which section 351 applies (section 
351 exchange) or to which section 361 applies by reason of a divisive 
reorganization that qualifies under sections 355 and 368(a)(1)(D), 
section 357(c)(1) generally provides that, if the sum of the amount of 
the transferor's liabilities assumed by the transferee corporation 
exceeds the total adjusted basis of the assets transferred by the 
transferor to the transferee corporation in the exchange, then such 
excess is considered as a gain from the sale or exchange of a capital 
asset or of property that is not a capital asset, as the case may be. 
See also section 368(a)(3)(C) (providing that a reorganization that 
would qualify under both section 368(a)(1)(D) and (G) is treated as 
qualifying under section 368(a)(1)(D) for purposes of section 
357(c)(1)).
    However, section 357(c)(2) provides that the general rule in 
section 357(c)(1) does not apply to any exchange (i) to which section 
357(b) applies, or (ii) that is pursuant to a plan of reorganization 
within the meaning of section 368(a)(1)(G) in which no former 
shareholder of the transferor receives any consideration for its stock. 
Rev. Rul. 2007-8, 2007-1 C.B. 469, holds that the general rule in 
section 357(c)(1) does not apply to a section 351 exchange if that 
transaction also qualifies as a reorganization described in section 
368(a)(1)(A), (C), (D) (provided the requirements of section 354(b)(1) 
are satisfied), or (G) (provided the requirements of section 354(b)(1) 
are satisfied).
    Furthermore, under section 357(c)(3), if the transferor transfers 
in a section 351 exchange (including a divisive reorganization that 
overlaps with a section 351 exchange; see section 357(c)(3) 
(referencing an exchange to which section 357(c)(1) applies)) a 
liability the payment of which either would give rise to a deduction or 
would be described in section 736(a) of the Code (concerning payments 
made in liquidation of the partnership interest of a retiring or 
deceased partner), the amount of such liability is excluded in 
determining the amount of liabilities assumed under section 357(c)(1) 
unless the incurrence of the liability resulted in the creation of (or 
an increase in) the basis of any property. In addition, liabilities the 
payment of which would give rise to a capital expenditure are not 
included for purposes of section 357(c)(1) unless the incurrence of the 
liability resulted in the creation of (or an increase in) the basis of 
any property. See Rev. Rul. 95-74, 1995-2 C.B. 36.

D. Section 361: Distributions to Shareholders of Target Corporation

1. Overview
    Section 361 is an operative provision applicable to certain 
exchanges and distributions of property in a transaction that satisfies 
the definitional requirements for qualification as a reorganization 
under section 368(a)(1). Section 361(a) and (b) provides the Federal 
income tax consequences to a target corporation (such as a distributing 
corporation in a divisive reorganization) that (i) is a party to a 
reorganization, and (ii) pursuant to the plan of reorganization, 
exchanges property with an acquiring corporation (such as a controlled 
corporation in a divisive reorganization) that also is a party to the 
reorganization. Section 361(c) provides the Federal income tax 
consequences to the target corporation (such as a distributing 
corporation in a divisive reorganization) of the distribution by the 
target corporation to its shareholders, or transfer to its creditors, 
of certain property in pursuance of or in

[[Page 5226]]

connection with the plan of reorganization that includes the exchange 
of property with an acquiring corporation (such as a controlled 
corporation in a divisive reorganization) that also is a party to the 
reorganization. See the discussion in part III.A of this Background 
(noting that the phrases ``in pursuance of'' and ``in connection with'' 
in section 361 convey the same meaning).
2. Enactment of Section 361(a): Purely Paper Transactions
    The original predecessor to current section 361(a) was enacted by 
Congress as part of section 202(b) of the Revenue Act of 1918 (Pub. L. 
65-254, 40 Stat. 1057, 1060 (1919)). The applicable part of section 
202(b) of the Revenue Act of 1918 was subsequently incorporated in 
section 112 of the 1939 Code before being adopted as section 361(a) of 
the 1954 Code and thereafter as current section 361(a).
    Congress enacted the applicable part of section 202(b) of the 
Revenue Act of 1918 ``to establish the rule for determining taxable 
gains in the case of exchanges of property and to negate the assertion 
of tax in the case of certain purely paper transactions.'' S. Rep. No. 
65-617, at 5 (1918). As stated in the legislative history, the 
substance of the original predecessor to section 361(a) is that (i) 
when property is exchanged for other property, the property received in 
the exchange should be treated as the equivalent of cash in the amount 
of its fair market value, but (ii) when, in connection with the 
reorganization or consolidation of a corporation, a person receives, in 
place of stock or securities, new stock or securities of no greater 
aggregate par value, or when a person receives, in place of property, 
stock of a corporation formed to take over such property, no gain or 
loss should be deemed to occur from the exchange. See id. at 5-6.
    More than a century after the enactment of its original 
predecessor, section 361(a) continues to provide generally that a 
corporation (that is, the target corporation) that is a party to a 
reorganization (such as the distributing corporation in a divisive 
reorganization) recognizes no gain or loss if it exchanges property 
pursuant to the plan of reorganization solely for stock and securities 
in another corporation (that is, the acquiring corporation) that is a 
party to the reorganization (such as a controlled corporation in a 
divisive reorganization).
3. Enactment of Section 361(b): Conduit for Distribution to 
Shareholders
    The original predecessor to current section 361(b) was enacted by 
Congress as section 203(e) of the Revenue Act of 1924 (Pub. L. 68-176, 
43 Stat. 253, 256). Section 203(e) of the Revenue Act of 1924 was 
subsequently incorporated in section 112 of the 1939 Code before being 
adopted as section 361(b) of the 1954 Code and thereafter as current 
section 361(b).
    Congress enacted section 203(e) of the Revenue Act of 1924 to 
provide that (i) if the corporation that sells its assets in connection 
with the reorganization ``acts merely as a conduit'' in passing the 
sale proceeds on to its shareholders, no gain to the corporation is to 
be recognized, but (ii) if the corporation ``retains the entire amount 
of proceeds with the result that the transaction is in substance a real 
sale, then the gain shall be recognized.'' S. Rep. No. 68-398, at 16 
(1924). This stated policy is reflected in current section 361(b)(1).
    Section 361(b)(1)(A) provides that, if section 361(a) would apply 
to an exchange but for the fact that the property received by the 
target corporation also includes money or other property, no gain will 
be recognized by the target corporation if it distributes the money or 
other property pursuant to the plan of reorganization. Congress has 
enacted no limitation on the aggregate amount of cash and the fair 
market value of other property that a target corporation can distribute 
to its shareholders (as opposed to creditors) under section 
361(b)(1)(A) (although section 368 limits the amount of money or other 
property that may be received in certain corporate reorganizations).
    Section 361(b)(1)(B), which reflects congressional intent with 
respect to a target corporation's failure to act solely as a conduit in 
distributing the sale proceeds (that is, money or other property) to 
its shareholders, provides that the target corporation (such as the 
distributing corporation in a divisive reorganization) recognizes gain 
in an amount that does not exceed the sum of the money and fair market 
value of the other property that the corporation fails to distribute 
pursuant to the plan of reorganization.
4. Section 361(c): Distributions of Appreciated Property to Target 
Corporation Shareholders
    Section 361(c) originally was enacted by Congress as section 
1804(g)(1) of the Tax Reform Act of 1986. As part of a wholesale 
rewrite of section 361, Congress amended section 361(c) by enacting 
section 1018(d)(5)(A) of the Technical and Miscellaneous Revenue Act of 
1988 (Pub. L. 100-647, 102 Stat. 3342, 3578) so that the statute 
``conforms the treatment of distributions of property by a corporation 
to its shareholders in pursuance of a plan of reorganization to the 
treatment of nonliquidating distributions (under section 311).'' S. 
Rep. No. 100-445, at 393 (1988).
    Section 311(a) generally provides that, except as provided in 
section 311(b) (concerning distributions of appreciated property), no 
gain or loss is recognized by a corporation on the distribution (not in 
complete liquidation) with respect to its stock of (i) its stock (or 
rights to acquire its stock), or (ii) property. Accordingly, section 
361(c)(1) generally provides that, except as provided in section 
361(c)(2) (concerning distributions of appreciated property), no gain 
or loss is recognized by a target corporation that is a party to a 
reorganization upon a distribution of property to its shareholders 
pursuant to a plan of reorganization.
    Consistent with section 311(b), section 361(c)(2)(A) provides that, 
if the target corporation distributes property other than qualified 
property in a distribution described in section 361(c)(1), and if the 
fair market value of that other property exceeds the corporation's 
adjusted basis in that other property, then gain is recognized by the 
target corporation as if the property were sold to the distributee at 
its fair market value. The term ``qualified property'' is defined in 
section 361(c)(2)(B) to mean (i) any stock, right to acquire stock, or 
obligation (including a security) of the corporation, and (ii) any 
stock, right to acquire stock, or obligation (including a security) of 
another corporation that is a party to the reorganization received by 
the target corporation in the exchange.
    Therefore, although a target corporation would recognize no gain on 
an exchange described in section 361(a) (section 361(a) exchange) if 
that corporation received appreciated non-qualified property and 
distributed that property to its shareholders pursuant to section 
361(b)(1)(A), that corporation nonetheless would recognize gain on the 
distribution to its shareholders under section 361(c)(2)(A). If any 
such property is subject to a liability, or if the shareholder assumes 
a liability of the target corporation in connection with the 
distribution, section 361(c)(2)(C) provides that the fair market value 
of that property is treated as not less than the amount of that 
liability for purposes of section 361(c)(2)(A).

[[Page 5227]]

5. Safe Harbors for Transfers to Creditors of the Distributing 
Corporation
    Congress added section 361(b)(3) and (c)(3) as part of the 
wholesale rewrite of section 361 in the Technical and Miscellaneous 
Revenue Act of 1988. Section 361(b)(3) provides that, for purposes of 
section 361(b)(1), any transfer of the money or other property received 
in the exchange by the target corporation to its creditors in 
connection with the reorganization is treated as a distribution 
pursuant to the plan of reorganization. Similarly, section 361(c)(3) 
provides that, for purposes of section 361(c), any transfer of 
qualified property by the target corporation to its creditors in 
connection with the reorganization is treated as a distribution to its 
shareholders pursuant to the plan of reorganization.
6. Response to Supreme Court's Decision in Minnesota Tea Company
    In Minnesota Tea Co. v. Helvering, 302 U.S. 609 (1938), the Supreme 
Court held that a distribution by a target corporation to its 
shareholders of cash received from an acquiring corporation in a 
reorganization was not a qualifying ``distribution'' for purposes of 
the predecessor to section 361(b)(1)(A), because the shareholders 
immediately used that distributed cash to pay the target corporation's 
creditors as part of a prearranged plan. Citing Gregory v. Helvering, 
293 U.S. 465, 469 (1935), as providing the ``controlling principle'' 
for its decision, the Court determined that the payment of 
indebtedness, and not the distribution of dividends, ``was, from the 
beginning, the aim of the understanding with the stockholders and was 
the end accomplished by carrying that understanding into effect.'' 
Minnesota Tea, 302 U.S. at 613-14. Because the Minnesota Tea Company 
``received the same benefit as though it had retained that amount from 
[the] distribution and applied it to the payment of such 
indebtedness,'' the Court concluded that the company failed to satisfy 
the predecessor to section 361(b)(1)(A). See id. at 613 (emphasis 
added).
    In describing the rationale for enacting section 361(b)(3) and 
(c)(3), the legislative history explains that each provision 
``overrules the holding in Minnesota Tea Company v. Helvering.'' S. 
Rep. No. 100-445, at 393 n.102 (1988); see also H.R. Rep. 100-795, at 
372 (1988). The legislative history described the substance of the safe 
harbor in section 361(b)(3) as providing that ``transfers of property 
to creditors in satisfaction of the corporation's indebtedness in 
connection with the reorganization are treated as distributions 
pursuant to the plan of reorganization for this purpose.'' S. Rep. No. 
100-445, at 393 (1988) (emphasis added). Likewise, the legislative 
history described the corresponding safe harbor in section 361(c)(3) as 
providing that ``the transfer of qualified property by a corporation to 
its creditors in satisfaction of indebtedness is treated as a 
distribution pursuant to the plan of reorganization.'' Id. (emphasis 
added). By treating transfers of property to creditors in satisfaction 
of indebtedness as distributions pursuant to the plan of 
reorganization, Congress balanced the dual policy objectives of (i) 
preserving consistency with the fundamental requirement of section 361 
that property be distributed, and (ii) enacting a provision to address 
transfers to creditors in satisfaction of indebtedness that overruled 
the holding in Minnesota Tea.
7. Adjusted Basis Limitation for Purposes of Section 361(b)(3)
    In the case of a divisive reorganization described in sections 355 
and 368(a)(1)(D), the third sentence in section 361(b)(3) (adjusted 
basis limitation) limits the extent to which a transfer of money or 
other property to a creditor is treated as a distribution pursuant to 
the plan of reorganization for the purposes of section 361. 
Specifically, section 361(b)(3) applies solely to the extent the sum of 
the money and the fair market value of the other property transferred 
to creditors of the distributing corporation does not exceed the 
aggregate adjusted bases of the assets transferred to the controlled 
corporation in the section 361(a) exchange, reduced by the amount of 
the distributing corporation's liabilities that the controlled 
corporation actually assumes within the meaning of section 357(c).
    Congress enacted the adjusted basis limitation in section 361(b)(3) 
as part of the American Jobs Creation Act of 2004 (Pub. L. 108-357, 118 
Stat. 1418) based on the concern stated in the legislative history that 
taxpayers had developed tax-planning strategies to circumvent the 
adjusted basis limitation in section 357(c) on actual assumptions by 
controlled corporations in divisive reorganizations. See S. Rep. No. 
108-192, at 185 (2003). Specifically, the committee report observed 
that a distributing corporation (i) could cause the controlled 
corporation to borrow money from a financial institution and transfer 
that money to the distributing corporation in the section 361(a) 
exchange, and then (ii) could use that money to pay its creditors. Id. 
The committee report concluded that, although this series of 
transactions does not involve an actual assumption by the controlled 
corporation within the meaning of section 357, it is ``economically 
similar to the actual assumption'' because, at the end of the series of 
transactions, the distributing corporation has reduced its indebtedness 
to its creditor and the controlled corporation has become indebted to a 
creditor (albeit a different creditor) for an equal amount. See id. 
Accordingly, ``because section 361(b) [did] not contain a limitation on 
the amount that can be distributed to creditors,'' Congress limited the 
scope of the section 361(b)(3) safe harbor to ``the amount of the basis 
of the assets contributed to a controlled corporation in a divisive 
reorganization.'' Id.
8. Express Grant of Authority
    As stated previously in the Authority section of this preamble, the 
second sentence of section 361(b)(3) provides the Secretary with an 
express grant of authority to prescribe such regulations as may be 
necessary to prevent avoidance of Federal income tax through abuse of 
the safe harbors in section 361(b)(3) and (c)(3). Congress included 
this grant of authority in section 361(b)(3) when Congress enacted both 
provisions as part of the Technical and Miscellaneous Revenue Act of 
1988.

III. Plan of Reorganization; Party to a Reorganization

A. Overview

    For more than a century, the ``plan of reorganization'' requirement 
has served to limit the application of the operative provisions in 
subchapter C solely to those transactions with a sufficiently proximate 
relationship to transactions that satisfy the definitional requirements 
in subchapter C for a reorganization (proximate relationship 
requirement). For example, see section 202(b) of the Revenue Act of 
1918 (providing that an exchange did not qualify for nonrecognition 
treatment unless the transaction was ``in connection with'' a 
reorganization). In other words, Congress has long viewed the proximate 
relationship requirement as an integral tool for preventing the 
nonrecognition provisions in subchapter C from applying to transactions 
to which general gain or loss provisions of the Code (for example, 
section 1001 of the Code) should apply.
    This long-standing congressional purpose is illustrated by the 
evolution of section 202(c)(1) of the Revenue Act

[[Page 5228]]

of 1921 (Pub. L. 67-98, 42 Stat. 227). That provision originally 
provided nonrecognition treatment for an exchange of property held for 
investment or for productive use in a trade or business, with no 
exception for stock or securities, and with no proximate relationship 
requirement. Tax advisors took advantage of this provision by 
structuring exchanges of portfolio investment securities for other 
securities in transactions that resulted in no recognition of Federal 
income tax. After receiving a request from the Treasury Department to 
address this abuse, Congress amended section 202(c)(1) by removing 
exchanges of stock and securities from nonrecognition treatment except 
for exchanges occurring in the context of a reorganization. See An Act 
to Amend the Revenue Act of 1921 in Respect to Exchanges of Property, 
Public Law 67-545, 42 Stat. 1560 (1923); J. Seidman, Legislative 
History of Federal Income Tax Laws: 1938-1861, at 798 (1938); see also 
Letter from A. W. Mellon, Secretary of the Treasury, to Congressman 
William R. Green, Acting Chairman of the Committee on Ways and Means 
(Jan. 13, 1923).
    Since first establishing the proximate relationship requirement, 
Congress has implemented that requirement through various linguistic 
formulations over time. However, Congress has indicated that such 
variations in language were not intended to reflect substantive 
differences. For example, Congress replaced ``in connection with'' in 
section 202(b) of the Revenue Act of 1918 with ``in the 
reorganization'' in section 202(c) of the Revenue Act of 1921. When 
describing section 202(c) of the Revenue Act of 1921, a congressional 
committee print explicitly referred to the proximate relationship under 
that section as requiring an ``in connection with'' relationship. See 
S. Comm. on Finance, 68th Cong., Statement of the Changes Made in the 
Revenue Act of 1921 by H.R. 6715 and the Reasons Therefor, at 5-6 
(Comm. Print 1924).
    In section 203(c) of the Revenue Act of 1924, Congress restated the 
proximate relationship requirement as requiring an ``in pursuance of a 
plan of reorganization'' relationship. This requirement, like the ``in 
connection with'' requirement, exists in the current definitional and 
operative provisions of subchapter C. The legislative history 
underlying section 203 of the Revenue Act of 1924 explicitly refers to 
the ``in pursuance of the plan of reorganization'' formulation in 
several instances as ``in connection with the reorganization.'' See 
H.R. Rep. No. 68-179, at 13-16 (1924). In particular, at one point, the 
Committee on Ways and Means described the change in formulation of the 
proximate relationship requirement as a result of ``minor changes in 
phraseology.'' See id. at 13.

B. Definition of ``Plan of Reorganization''

    The term ``plan of reorganization'' is not defined in subchapter C. 
Instead, the sole authoritative guidance defining this term is set 
forth in the Income Tax Regulations. Specifically, Sec.  1.368-2(g) 
provides that the term ``plan of reorganization'' refers to a 
``consummated transaction specifically defined as a reorganization 
under section 368(a),'' and that ``[s]ection 368(a) contemplates 
genuine corporate reorganizations which are designed to effect a 
readjustment of continuing interests under modified corporate forms.'' 
Section 1.368-2(g) further provides that the term ``plan of 
reorganization'' ``is not to be construed as broadening the definition 
of reorganization as set forth in section 368(a),'' but rather ``is to 
be taken as limiting the nonrecognition of gain or loss to such 
exchanges or distributions as are directly a part of the transaction 
specifically described as a reorganization in section 368(a).'' Section 
1.368-2(g) further provides that the transaction (or series of 
transactions) ``embraced in a plan of reorganization must not only come 
within the specific language of section 368(a),'' but also that ``the 
readjustments involved in the exchanges or distributions effected in 
the consummation [of the plan of reorganization] must be undertaken for 
reasons germane to the continuance of the business of a corporation a 
party to the reorganization.''
    However, significant uncertainty and confusion have arisen 
regarding the scope, purpose, and application of Sec.  1.368-2(g). As 
expressed by the Tax Court in an observation often referenced by courts 
and commentators, ``the above definition is imbued with qualities of 
flexibility and vagueness, with the result that it does not present 
precise self-executing guidelines.'' Int'l Telephone & Telegraph Corp. 
v. Comm'r, 77 T.C. 60, 75 (1981); see also J.E. Seagram Corp. v. 
Comm'r, 104 T.C. 75, 96 (1995) (relying on the quote in Int'l Telephone 
in observing that Sec.  1.368-2(g) provides ``substantial 
elasticity''). As a result, Sec.  1.368-2(g) (including its proximate 
relationship requirement) has created significant uncertainty and 
confusion for taxpayers and the IRS in determining the scope of 
transactions that properly should be taken into account for purposes of 
applying the definitional and operative provisions of subchapter C.
    Section 1.368-1(c) further describes the ``plan of reorganization'' 
concept and provides important context regarding the application of 
this concept and its embedded proximate relationship requirement. 
Specifically, Sec.  1.368-1(c) provides, in part, that ``[t]he 
provisions of [part III of subchapter C] referred to in this paragraph 
are inapplicable unless there is a plan of reorganization'' (emphasis 
added). Section 1.368-1(c) further provides that ``[a] plan of 
reorganization must contemplate the bona fide execution of one of the 
transactions specifically described as a reorganization in section 
368(a) and for the bona fide consummation of each of the requisite acts 
under which nonrecognition of gain is claimed.'' That transaction, and 
those acts, must be an ``ordinary and necessary incident of the conduct 
of the enterprise and must provide for a continuation of the 
enterprise.'' Id. Finally, Sec.  1.368-1(c) provides that a scheme 
involving ``an abrupt departure from normal reorganization procedure in 
connection with a transaction on which the imposition of tax is 
imminent, such as a mere device that puts on the form of a corporate 
reorganization as a disguise for concealing its real character, and the 
object and accomplishment of which is the consummation of a 
preconceived plan having no business or corporate purpose, is not a 
plan of reorganization.''
    Consistent with the discussion in part III.A of this Background, 
Sec.  1.368-1(c) reflects the function of the ``plan of 
reorganization'' concept and its embedded proximate relationship 
requirement--namely, to limit the application of the definitional and 
operative provisions of subchapter C to those transactions included in 
the plan of reorganization. Section 1.368-1(c) also requires all 
transactions properly included in the plan of reorganization to be 
consistent with, and to facilitate satisfaction of, a principal 
requirement for nonrecognition treatment under the reorganization 
provisions of subchapter C (that is, the continuation of an 
enterprise). Finally, Sec.  1.368-1(c) reflects that devices and sham 
transactions cannot properly be included in a plan of reorganization.

C. Party to a Reorganization

    Section 368(b) generally provides that the term ``a party to a 
reorganization'' includes (i) a corporation resulting from a 
reorganization, and (ii) both corporations, in the case of a 
reorganization resulting from the

[[Page 5229]]

acquisition by one corporation of stock or properties of another. 
Consistent with section 368(b), Sec.  1.368-2(f) defines the term 
``party to a reorganization'' as including ``a corporation resulting 
from a reorganization, and both corporations in a transaction 
qualifying as a reorganization where one corporation acquires stock or 
properties of another corporation.'' Section 1.368-2(f) further 
articulates which entities are parties to a reorganization in various 
types of reorganizations defined in section 368(a)(1). However, the 
uncertainty regarding the meaning of ``plan of reorganization,'' 
described in part III.B of this Background, has resulted in confusion 
regarding the proper identification of parties to a reorganization.

D. Reporting and Recordkeeping Requirements for Corporate 
Reorganizations

    Section 1.368-3 sets forth reporting and recordkeeping requirements 
for corporate reorganizations. Section 1.368-3(a) requires a plan of 
reorganization to be adopted by each corporation that is a party to the 
reorganization, and it requires each such corporation to include a 
statement with its Federal income tax return that includes certain 
limited information about the reorganization. However, Sec.  1.368-3(a) 
provides no additional detail on the manner in which the plan of 
reorganization must be adopted, and it does not require the plan of 
reorganization to be reflected in any documentation or records of the 
parties to the reorganization.
    Current Sec.  1.368-3(a) contrasts starkly with a prior version of 
Sec.  1.368-3(a), which provided that the plan of reorganization ``must 
be adopted by each of the corporations parties thereto; and the 
adoption must be shown by the acts of its duly constituted responsible 
officers, and appear upon the official records of the corporation.'' 
See Sec.  1.368-3(a) (effective from November 26, 1960, to May 29, 
2006) (prior Sec.  1.368-3(a)).
    Prior Sec.  1.368-3(a) also imposed additional requirements to 
facilitate the IRS's administration of the reorganization provisions in 
part III of subchapter C. In particular, prior Sec.  1.368-3(a) 
required the parties to a reorganization to file with the IRS a ``copy 
of the plan of reorganization, together with a statement, executed 
under the penalties of perjury, showing in full the purposes thereof 
and in detail all transactions incident to, or pursuant to, the plan.'' 
In contrast, taxpayers currently are not required by Sec.  1.368-3 to 
provide as part of their Federal income tax return a plan of 
reorganization that describes the transactions to which taxpayers 
intend to apply the nonrecognition provisions of subchapter C.
    In addition, prior Sec.  1.368-3(a) required taxpayers to file with 
the IRS ``a complete statement of all facts pertinent to the 
nonrecognition of gain or loss in connection with the reorganization.'' 
Current Sec.  1.368-3(a) contains no such requirement. Therefore, the 
IRS currently does not receive as part of a taxpayer's Federal income 
tax return a statement of facts necessary to determine the proper 
application of the nonrecognition provisions of subchapter C to the 
transactions comprising a corporate reorganization.
    Instead, current Sec.  1.368-3(a) merely requires each corporate 
party to a reorganization to include a statement, on or with its return 
for the taxable year of the exchange, that includes: (i) the names and 
employer identification numbers (if any) of all such parties; (ii) the 
date of the reorganization; (iii) the value and basis of the assets, 
stock, or securities of the target corporation transferred in the 
transaction, determined immediately before the transfer in the manner 
described in Sec.  1.368-3(a); and (iv) the date and control number of 
any one or more private letter rulings issued by the IRS in connection 
with the reorganization. Current Sec.  1.368-3(b) imposes similar 
requirements on significant holders of stock or securities of the 
target corporation.
    Like prior Sec.  1.368-3(c), current Sec.  1.368-3(d) requires 
taxpayers to retain their permanent records with respect to a corporate 
reorganization.

IV. TIGTA Report To Improve Enforcement of Corporate M&A Transactions

    In 2019, the Treasury Inspector General for Tax Administration 
(TIGTA) published a report titled ``A Strategy Is Needed to Assess the 
Compliance of Corporate Mergers and Acquisitions With Federal Tax 
Requirements,'' Ref. No. 2019-30-050 (Sept. 5, 2019) (TIGTA Report). In 
that report, TIGTA considered the scope of information required to be 
provided under Sec.  1.368-3(a) and expressed that ``the forms 
previously detailed represent only a small portion of the information 
that may be filed, and certain forms used to report merger and 
acquisition (M&A) transactions may not be providing sufficient 
information to identify noncompliance.'' Id. at 14-15.
    Accordingly, TIGTA recommended that, if the IRS finds that the 
current forms do not contain information sufficient for identifying 
potential noncompliance in M&A transactions, the IRS ``should consider 
amending the filing criteria and information required in the forms to 
develop useful compliance tools.'' Id. at 14. The IRS agreed with this 
recommendation, stating that it will continue to consider how to use 
M&A transaction information in its compliance efforts.

V. Reporting Requirements for Section 355 Transactions

    In a notice of proposed rulemaking (REG-116085-23) published 
elsewhere in the Proposed Rules section of this issue of the Federal 
Register, the Treasury Department and the IRS are issuing proposed 
regulations to revise current Sec.  1.355-5 (proposed Sec.  1.355-5) to 
enhance the IRS's ability to administer and enforce the requirements of 
section 355. Similar to current Sec.  1.368-3 (previously discussed in 
part III.D of this Background), current Sec.  1.355-5 requires the 
distributing corporation and each significant distributee (as defined 
in current Sec.  1.355-5(c)(1)) to include a statement with its tax 
return that includes certain limited information about the section 355 
transaction. To implement the recommendation in the TIGTA Report 
described in part IV of this Background, proposed Sec.  1.355-5 would 
require taxpayers to submit new IRS Form 7216, Multi-Year Reporting 
Related to Section 355 Transactions (or any successor form), to provide 
the IRS with additional information to help the IRS identify potential 
noncompliance in section 355 transactions.

VI. Revenue Procedure 2024-24 and Notice 2024-38

    On May 2, 2024, the Treasury Department and the IRS released Rev. 
Proc. 2024-24, 2024-21 I.R.B. 1214, to provide procedures for 
requesting private letter rulings from the IRS regarding certain 
matters relating to section 355 transactions. Rev. Proc. 2024-24 
superseded Rev. Proc. 2018-53, 2018-43 I.R.B. 667, and made several 
significant changes to the requirements of that revenue procedure and 
to Rev. Proc. 2017-52, 2017-41 I.R.B. 283.
    Also on May 2, 2024, the Treasury Department and the IRS released 
Notice 2024-38, 2024-21 I.R.B. 1211, to describe their views and 
concerns relating to certain matters addressed in Rev. Proc. 2024-24, 
and to solicit feedback on the provisions set forth in Rev. Proc 2024-
24. In section 2.01 of Notice 2024-38, the Treasury Department and the 
IRS requested that such feedback take into account the

[[Page 5230]]

following three objectives for potential future guidance: (i) the 
guidance will be consistent with all relevant provisions of the Code 
(compliance objective); (ii) the guidance will provide certainty to 
taxpayers and the IRS regarding the application of all relevant 
provisions of the Code to purported section 355 transactions (increased 
certainty objective); and (iii) the guidance will be responsive to the 
manner in which section 355 transactions are engaged in by taxpayers 
and reflect current market practices and preferences (transaction 
facilitation objective), to the extent that such approach does not 
conflict with the first two objectives.

Explanation of Provisions

    The purpose of these proposed regulations is to establish a 
comprehensive set of rules to implement certain core definitional and 
operative provisions of subchapter C that address corporate 
separations, incorporations, and reorganizations. The current 
regulatory framework underlying these provisions is incomplete, 
outdated, and not reflective of their importance to the Federal 
corporate income tax system, given the trillions of dollars of 
corporate transactions governed by these statutory provisions. Due to 
the lack of up-to-date regulatory guidance, taxpayers and the IRS must 
rely on a patchwork of caselaw, IRS revenue rulings and revenue 
procedures, and non-authoritative IRS documents to discern the current 
state of the law with respect to these core provisions of subchapter C.
    Accordingly, providing comprehensive regulatory guidance to 
facilitate the implementation of these core definitional and operative 
provisions of subchapter C would promote taxpayer certainty and sound 
tax administration. Although Notice 2024-38 focused on Federal income 
tax issues regarding section 355 transactions, these core definitional 
and operative provisions also address incorporations and acquisitive 
reorganizations. Therefore, the proposed regulations would implement 
those statutory provisions for all corporate M&A transactions, in a 
manner that reflects the three objectives described in section 2.01 of 
Notice 2024-38 (that is, the compliance objective, the increased 
certainty objective, and the transaction facilitation objective) in 
accordance with their respective priorities as set forth therein.
    A principal objective of the Treasury Department and the IRS in 
issuing these proposed regulations is to significantly improve 
horizonal equities among taxpayers and tax advisors. In other words, 
based on feedback from tax advisors, the lack of authoritative guidance 
in this area effectively has transformed a taxpayer's option to request 
a private letter ruling on the application of certain definitional and 
operative provisions into a requirement. Indeed, tax advisors have 
directly reached out to the Treasury Department and the IRS to 
emphasize the mandatory nature of private letter rulings on certain 
topics in this area because, based on the current state of 
authoritative guidance, those tax advisors could not provide tax 
opinions at a sufficient level of comfort in the absence of a private 
letter ruling. Therefore, these tax advisors have stressed the 
importance of engaging in bar association panels and other professional 
speaking engagements to access the perspectives of Treasury Department 
and IRS officials regarding the government's current views on certain 
fundamental corporate tax issues.
    These proposed regulations would provide, through publicly 
accessible authoritative guidance, core definitional and operative 
provisions. This guidance is intended to facilitate the ability for 
taxpayers to achieve increased comfort on the Federal income tax 
treatment of their corporate M&A transactions without the need for a 
private letter ruling. Just as importantly, this guidance is intended 
to encourage the submission of private letter ruling requests and 
facilitate the IRS private letter ruling process. In particular, these 
proposed regulations are intended to help direct the focus of tax 
advisors to those issues that raise significant Federal income tax 
compliance concerns, and consequently improve the organization and 
focus of their private letter ruling submissions. Similarly, these 
proposed regulations are intended to increase the efficiency of the 
private letter ruling program by allowing submission reviewers to focus 
primarily on such significant issues, rather than those issues that 
would be addressed directly by this guidance.
    In explaining the provisions of these proposed regulations, this 
Explanation of Provisions discusses issues described in Notice 2024-38 
and the feedback received in response to Notice 2024-38. Such feedback 
has informed the development of these proposed regulations. This 
Explanation of Provisions also references proposed regulations, 
published elsewhere in the Proposed Rules section of this issue of the 
Federal Register, that would implement enhanced reporting requirements 
for section 355 transactions. Those enhanced reporting requirements are 
integral to the proposed substantive guidance set forth in these 
proposed regulations. Specifically, as described further in this 
Explanation of Provisions, this proposed substantive guidance reflects 
the long-standing reality that corporate transactions typically are 
carried out over multiple taxable years. The increased transactional 
flexibility that would be provided by these proposed regulations is 
conditioned on the IRS's ability to track the execution of these 
transactions throughout their lifecycle, and the enhanced reporting 
requirements for section 355 transactions would facilitate the IRS's 
ability to carry out its administrative function with respect to these 
transactions.

I. Distinction Between Delayed Distributions and Retentions; Rules for 
Qualifying Retentions

A. Notice 2024-38

    Section 2.02(1) of Notice 2024-38 stated the view of the Treasury 
Department and the IRS that the Code provides separate and distinct 
treatment for three instances in which a distributing corporation 
temporarily continues to hold controlled corporation stock or 
securities following the date on which the distributing corporation has 
distributed an amount of controlled corporation stock constituting 
control (within the meaning of section 368(c)) (control distribution 
date). These three instances are: (i) a delayed distribution of 
controlled corporation stock or securities that is ``part of the 
distribution'' (within the meaning of section 355(a)(1)(D)); (ii) a 
delayed distribution of controlled corporation stock or securities that 
is ``in pursuance of the plan of reorganization'' (within the meaning 
of section 361); and (iii) a retention of controlled corporation stock 
or securities.
    Section 2.02(2) of Notice 2024-38 stated the view of the Treasury 
Department and the IRS that section 355(a)(1)(D) effectively creates a 
rebuttable presumption that any retention evidences a plan to achieve a 
Federal income tax avoidance purpose. Section 2.02(2) of Notice 2024-38 
also stated that the Treasury Department and the IRS are considering 
the degree to which connections between the distributing corporation 
and the controlled corporation (and, as appropriate, the DSAG and the 
CSAG) after the control distribution date would prevent a transaction 
from qualifying under section 355. (The terms ``DSAG'' and ``CSAG'' 
mean the separate affiliated group (as defined in section 355(b)(3)(B)) 
of which the distributing

[[Page 5231]]

corporation or the controlled corporation, respectively, is the common 
parent.)
    Section 2.02(2) of Notice 2024-38 also stated the view of the 
Treasury Department and the IRS that overlapping directors, officers, 
or key employees and the existence of continuing contractual agreements 
between the distributing corporation (and other members of the DSAG) 
and the controlled corporation (and other members of the CSAG) that 
include provisions that are not arm's-length weigh against a 
determination of qualification under section 355.

B. Stakeholder Input

1. Existence of Rebuttable Presumption Under Section 355(a)(1)(D)(ii)
    As an initial matter, some stakeholders have contended that section 
355(a)(1)(D)(ii) does not create a rebuttable presumption that a 
retention evidences a plan with a principal purpose of avoiding Federal 
income tax, notwithstanding the explicit statutory requirement that the 
Secretary must be satisfied that such a purpose does not exist. 
Instead, these stakeholders have asserted that Congress's intent in 
including the ``no tax avoidance purpose'' language in section 
355(a)(1)(D)(ii) is unclear, and that the legislative history of 
section 355 does not give further details about the meaning of this 
language.
    Accordingly, these stakeholders have suggested that, rather than 
include a rebuttable presumption, the proposed regulations should place 
greater emphasis on (i) an examination of the corporate business 
purpose for the section 355 transaction, and (ii) a determination of 
whether the retained controlled corporation stock is disposed of as 
``part of the distribution'' (see section 355(a)(1)(D)) or ``in 
pursuance of the plan of reorganization'' (see section 361(c)). These 
stakeholders contend that their view is supported by sections 354, 355, 
and 361, as well as by Sec.  1.368-2(g), which requires readjustments 
involved in the exchanges or distributions effected in consummating a 
plan of reorganization to be ``undertaken for reasons germane to the 
continuance of the business of a corporation a party to the 
reorganization.''
2. Application of Plan of Reorganization With Regard to Section 
355(a)(1)(D)(ii)
    Stakeholders also have requested clarification in the proposed 
regulations that all delayed distributions, whether before or after the 
control distribution date, are treated as part of the distribution 
(within the meaning of section 355(a)(1)(D)) if they are effectuated 
pursuant to the plan of reorganization. Relatedly, stakeholders have 
recommended that the proposed regulations employ the same standard 
(that is, the same level of proximate relationship) in considering 
whether a transaction is ``part of the distribution'' and ``in 
pursuance of a plan of reorganization.'' Stakeholders have further 
requested confirmation in the proposed regulations that the ``no tax 
avoidance purpose'' requirement in section 355(a)(1)(D)(ii) applies 
only to the extent a delayed distribution fails to qualify under the 
operative provisions.
    Based on their analogy to their view of the ``plan of 
reorganization'' concept, these stakeholders have contended that the 
``as part of the distribution'' requirement in section 355(a)(1)(D) 
provides substantial flexibility to the distributing corporation 
regarding the timing and manner of dispositions of controlled 
corporation stock (for example, in a delayed distribution of controlled 
corporation stock to shareholders of the distributing corporation). In 
this regard, stakeholders have recommended that the phrase ``as part of 
the distribution'' be interpreted to provide section 355 qualification 
for situations in which the distributing corporation contemplates--but 
provides no further level of commitment to--a spectrum of potential 
dispositions of controlled corporation stock, so long as the 
distributing corporation eventually achieves one or more of those 
contemplated possibilities or related variants. As described by such 
stakeholders, the distributing corporation need not identify the timing 
of those dispositions (regardless of whether they span multiple taxable 
years of the distributing corporation), the potential recipients of 
controlled corporation stock (for example, creditors of the 
distributing corporation), or the method of disposing of that stock.
    The stakeholder input described in the foregoing paragraphs 
ultimately focuses on two aspects of the IRS private letter ruling 
program for section 355 transactions: (i) the requirement set forth in 
section 3.03(3)(a)(ii) of Rev. Proc. 2024-24 (the so-called ``pick a 
lane'' requirement); and (ii) the elimination under that revenue 
procedure of so-called ``backstop retention rulings.''
    With regard to the ``pick a lane'' requirement, these stakeholders 
read section 3.03(3)(a)(ii) of Rev. Proc. 2024-24 as providing that the 
IRS will entertain a request for rulings that: (i) a delayed 
distribution of controlled corporation stock or securities will be, as 
applicable, ``part of the distribution'' (within the meaning of section 
355(a)(1)(D)) or ``in pursuance of the plan of reorganization'' (within 
the meaning of section 361); and (ii) a retention of controlled 
corporation stock or securities that is not included in a ruling 
request described in clause (i) of this sentence will not be in 
pursuance of a plan having as one of its principal purposes the 
avoidance of Federal income tax (within the meaning of section 
355(a)(1)(D)(ii)). Stakeholders have further stated that, to comply 
with the so-called ``pick a lane'' requirement, a taxpayer must specify 
the portions of controlled corporation stock remaining after the 
control distribution (i) to which the taxpayer intends section 361(c) 
to apply, and (ii) which the taxpayer intends to retain and not dispose 
of under section 361(c). See section 3.03(3)(d) of Rev. Proc. 2024-24.
    In practice, the ``pick a lane'' requirement requires a taxpayer to 
identify to the IRS those transactions that the taxpayer intends to 
carry out as part of its plan of reorganization. However, stakeholders 
have contended that this requirement is problematic because Rev. Proc. 
2024-24 also has eliminated the availability of ``backstop retention 
rulings,'' which stakeholders have described as ``protective rulings'' 
affording taxpayers a determination by the IRS, before the first step 
of a divisive reorganization, that a retention at no point will have 
failed to satisfy the ``no tax avoidance purpose'' requirement in 
section 355(a)(1)(D)(ii).
    Stakeholders have contended that these changes in private letter 
ruling policy, combined with the requirement that all controlled 
corporation stock or securities be distributed within 12 months of the 
date of the first distribution (first distribution date) to receive a 
ruling that the distribution qualifies for nonrecognition treatment 
under section 355 (see section 3.03(2)(b)(ii) of Rev. Proc. 2024-24), 
have created an unnecessary risk for taxpayers that an intended 
divisive reorganization could fail to qualify under section 355 
(section 355(a)(1)(D)(ii) risk). For purposes of these proposed 
regulations, the term ``first distribution'' means the earliest 
distribution in a series of distributions made pursuant to the plan of 
distribution or plan of reorganization, as appropriate.
    Specifically, these stakeholders have asserted that, because 
transactions intended to qualify for nonrecognition treatment under 
section 361(c) often require most of a year to complete, tax advisors 
now are faced with three undesirable options. First, tax advisors could 
recommend the premature

[[Page 5232]]

termination of such transactions, which otherwise would have been 
effectuated for bona fide business purposes for corporate taxpayers. 
Second, tax advisors could attempt, in an unreasonably short timeframe, 
to receive from the IRS a supplemental private letter ruling that the 
``springing retention'' (that is, a retention that arises unexpectedly 
during the 12-month period) satisfies the ``no tax avoidance purpose'' 
requirement. Third, tax advisors could provide an opinion that the 
springing retention satisfies the ``no tax avoidance purpose'' 
requirement, notwithstanding the lack of authoritative guidance on that 
issue.

C. Proposed Regulations

    Consistent with the statement in section 2.02(2) of Notice 2024-38, 
proposed Sec.  1.355-10(c)(1) would reflect the presumption that a 
retention is pursuant to a plan having as one of its principal purposes 
the avoidance of Federal income tax. However, the Treasury Department 
and the IRS appreciate the views of stakeholders regarding delayed 
distributions and retentions. In particular, the Treasury Department 
and the IRS are sensitive to the potential negative impacts of the 
``pick a lane'' requirement and related requirements in Rev. Proc. 
2024-24 on divisive reorganizations, and to the lack of clear, 
authoritative guidance regarding the ``no tax avoidance purpose'' 
requirement of section 355(a)(1)(D)(ii). Therefore, and consistent with 
the compliance, increased certainty, and transaction facilitation 
objectives of these proposed regulations, the Treasury Department and 
the IRS have proposed rules to address the uncertainty highlighted by 
stakeholders in a manner that facilitates the ability of (i) taxpayers 
to carry out bona fide section 355 transactions, and (ii) the IRS to 
ensure that such transactions comply with all requirements of the Code.
1. Proposed Safe Harbor To Address Section 355(a)(1)(D)(ii) Risk
a. Overview
    In response to stakeholder concerns regarding the section 
355(a)(1)(D)(ii) risk, these proposed regulations would provide a safe 
harbor that incorporates objectively verifiable conditions for 
retentions not to be treated as pursuant to a plan having as one of its 
principal purposes the avoidance of Federal income tax (qualifying 
retentions). The Treasury Department and the IRS have proposed this 
safe harbor to enable taxpayers to satisfy the requirements of section 
355(a)(1)(D)(ii) with greater certainty even in the absence of a 
private letter ruling from the IRS--thereby achieving an increased 
certainty and transaction facilitation objectives. For taxpayers that 
do not satisfy the requirements of the proposed safe harbor, the 
proposed regulations would provide for a general facts-and-
circumstances determination for whether a retention is a qualifying 
retention.
b. Section 355(a)(1)(D)(ii) Safe Harbor
    Under the section 355(a)(1)(D)(ii) safe harbor in proposed Sec.  
1.355-10(c)(3), a distributing corporation would be treated as 
satisfying the general facts-and-circumstances test in proposed Sec.  
1.355-10(c)(2)(ii) for a qualifying retention if all six of the 
following conditions are satisfied. First, the distributing corporation 
must have a specific corporate business purpose for the retention as of 
the date of adoption of the plan of distribution or plan of 
reorganization, as appropriate, and at all times during the period of 
retention. Second, stock of the controlled corporation must be widely 
held during the period of retention after the first distribution date. 
Third, any overlap between the officers, directors, or key employees of 
the DSAG and of the CSAG must be limited in the manner described in 
proposed Sec.  1.355-10(c)(3)(iv). Fourth, any continuing arrangements 
between the distributing corporation and the controlled corporation 
during the period of retention either (i) must be negotiated on and 
reflect arm's-length terms, or (ii) within two years after the first 
distribution date, must be terminated or renegotiated to reflect arm's-
length terms. Fifth, the plan of distribution or plan of 
reorganization, as appropriate, must reflect a definite intent in the 
official records of the distributing corporation that the distributing 
corporation dispose of all retained controlled corporation stock (or 
securities) by the end of the five-year period beginning on the first 
distribution date. Sixth, the disposition of retained controlled 
corporation stock (or securities) must not result in less Federal 
income tax to the distributing corporation (determined based on the 
fair market value and adjusted basis of that stock (or securities) as 
of the first distribution date) than if that stock (or securities) had 
been distributed in the first distribution. The distributing 
corporation must include in its plan of distribution or plan of 
reorganization (as applicable) a description of each agreement and 
transaction that establishes the satisfaction of the foregoing six 
conditions.
c. Rationale for Section 355(a)(1)(D)(ii) Safe Harbor
    The safe harbor in proposed Sec.  1.355-10(c)(3) is intended to 
balance taxpayers' need for certainty with the IRS's need to ensure 
taxpayer compliance with section 355(a)(1)(D)(ii). As discussed in part 
IV of the Background, TIGTA recommended that the IRS consider amending 
the filing criteria and information required in current forms to 
develop useful compliance tools. The inclusion of objective 
requirements in the section 355(a)(1)(D)(ii) safe harbor is consistent 
with both TIGTA's recommendation and the compliance, increased 
certainty, and transaction facilitation objectives for guidance 
described in section 2.01 of Notice 2024-38.
    Moreover, under proposed Sec.  1.355-5 and new IRS Form 7216 (see 
part V of the Background), and consistent with the recommendation in 
the TIGTA Report, a taxpayer would be required to report key 
information that would enable the IRS to ensure that the taxpayer, 
during each taxable year of the retention period, continues to comply 
with the requirements of the section 355(a)(1)(D)(ii) safe harbor. 
Thus, the section 355(a)(1)(D)(ii) safe harbor, coupled with the 
enhanced reporting requirements for section 355 transactions, would 
increase taxpayer certainty (by reducing the so-called section 
355(a)(1)(D)(ii) risk) and would facilitate IRS administration of 
section 355(a)(1)(D)(ii). The Treasury Department and the IRS are of 
the view that these two proposals would significantly help achieve all 
three objectives of these proposed regulations.
    The proposed regulations would not incorporate the stakeholders' 
recommendation that the requirements of section 355(a)(1)(D)(ii) be 
treated as satisfied so long as the distributing corporation disposes 
of all controlled corporation stock pursuant to the plan of 
reorganization. Such an approach would conflict with long-standing 
Sec.  1.355-2(e)(2), which requires the consideration of factors aside 
from the manner in which the distributing corporation disposes of its 
retained controlled corporation stock (for example, if the distribution 
would be treated to any extent as a distribution of ``other property'' 
under section 356). The stakeholders' recommendation would not be 
consistent with section 355(a)(1)(D)(ii), because that recommendation, 
by itself, would not ensure a genuine separation.
    In addition, the proposed regulations would not incorporate 
stakeholders' recommendation that a strong corporate

[[Page 5233]]

business purpose for a section 355 transaction be treated as sufficient 
to satisfy the requirements under section 355(a)(1)(D)(ii). This 
suggestion is inconsistent with the plain reading of the statute, which 
requires a determination that the avoidance of Federal income tax was 
not a principal purpose of the retention. In other words, the 
distributing corporation could possess a strong corporate business 
purpose for the section 355 transaction in general and for the 
retention in particular, and yet also possess a principal purpose for 
the retention of avoiding Federal income tax.
    Ultimately, the stakeholders' recommended approaches would conflict 
with the purpose of section 355(a)(1)(D), which is to ensure genuine 
separations between the distributing and controlled corporations--a 
policy reflected in the legislative history of section 355(a)(1)(D) and 
the long-standing view of the Treasury Department and the IRS regarding 
that purpose as fundamental to all section 355 transactions. The 
legislative history of section 355(a)(1)(D) indicates that Congress's 
initial preference was to provide no exception to the complete-
distribution requirement under section 355(a)(1)(D)(i), and that the 
exception for retentions originated through a subsequent Senate 
amendment. See H.R. Rep. No. 83-1337, at A121 (1954); S. Rep. No. 83-
1622, at 266 (1954). Indeed, Treasury regulations that predated the 
enactment of section 355(a)(1)(D), and that tax advisors have 
acknowledged as the basis for section 355(a)(1)(D), provided that the 
business reasons supporting a distribution of controlled corporation 
stock ordinarily required the distribution of all controlled 
corporation stock owned by the distributing corporation. See Sec.  
29.112(b)(11)-2(c) of Regulation 111 (issued under section 112(b)(11) 
of the 1939 Code, the predecessor to section 355 of the 1954 Code); see 
also Sec.  1.355-2(e)(2), which continues to reflect this language). 
Long-standing revenue rulings and general counsel memoranda also 
reflect the view that, under the plain reading of section 
355(a)(1)(D)(ii), Congress intended to subject retentions to heightened 
scrutiny to ensure that the section 355 transaction effectuates a 
genuine separation of the distributing corporation and the controlled 
corporation. See Rev. Rul. 75-469; Rev. Rul. 75-321; see also G.C.M. 
32136 (Oct. 23, 1961).
2. Facts-and-Circumstances Test for Determining Compliance With Section 
355(a)(1)(D)(ii)
    If a taxpayer fails to satisfy the requirements of the section 
355(a)(1)(D)(ii) safe harbor in proposed Sec.  1.355-10(c)(3), the 
taxpayer may establish compliance with section 355(a)(1)(D)(ii) through 
satisfaction of the facts-and-circumstances test in proposed Sec.  
1.355-10(c)(2)(ii). As with qualification for the proposed section 
355(a)(1)(D)(ii) safe harbor, satisfaction of the proposed facts-and-
circumstances test would require a determination that the distributing 
corporation and the controlled corporation have genuinely separated, 
among other requirements. This proposed facts-and-circumstances 
approach combined with the proposed safe harbor would provide taxpayers 
and the IRS with increased certainty regarding the application of 
section 355(a)(1)(D)(ii).
    Under the facts-and-circumstances approach of proposed Sec.  1.355-
10(c)(2)(ii), the distributing corporation first must establish that 
the distribution resulted in a genuine separation of the DSAG and the 
CSAG. Second, the distributing corporation must establish that the 
retention does not allow the DSAG to retain any practical control over 
the CSAG. Third, there must be a sufficient corporate business purpose 
for the retention as of the date the plan of distribution or the plan 
of reorganization (as applicable) is adopted. Fourth, there must be a 
sufficient corporate business purpose for the retention at all times 
during the period of retention. Fifth, the disposition of retained 
controlled corporation stock (or securities) must not result in less 
Federal income tax to the distributing corporation (determined based on 
the fair market value and adjusted basis of that stock (or securities) 
as of the first distribution date) than if that stock (or securities) 
had been distributed in the first distribution.
    Consistent with the views set forth in section 2.02(2) of Notice 
2024-38, the existence of (i) overlapping officers, directors, or key 
employees between the DSAG and the CSAG, and (ii) non-arm's-length 
continuing contractual agreements between the DSAG and the CSAG, would 
be facts and circumstances indicating that the retention fails the 
requirements under section 355(a)(1)(D)(ii). For purposes of proposed 
Sec.  1.355-10(c)(2)(ii), the relative weight of those indicia would 
depend upon all facts and circumstances, including the corporate 
business purpose for the section 355 transaction. For example, such 
continuing relationships particularly would weigh against a 
determination that the retention satisfies the requirements under 
section 355(a)(1)(D)(ii) if the purported corporate business purpose 
for the section 355 transaction is so-called ``fit and focus'' (that 
is, a separation to enhance the success of the separated businesses by 
resolving management, systemic, or other problems that arise by virtue 
of the distributing corporation's operation of different businesses 
within a single corporation or affiliated group).
3. Consistent Voting Requirements
    Regardless of whether a section 355 transaction qualifies for the 
section 355(a)(1)(D)(ii) safe harbor, if the section 355 transaction 
involves a retention, proposed Sec.  1.355-10(c)(2)(iii) would require 
the DSAG to vote any retained controlled corporation stock in 
proportion to the votes cast by the controlled corporation's other 
shareholders (other than persons related to the distributing 
corporation). This proposed requirement is consistent with the long-
standing position of the Treasury Department and the IRS with regard to 
section 355(a)(1)(D)(ii), as expressed through several revenue rulings, 
revenue procedures, and other sub-regulatory guidance.
4. Plan of Distribution
    Consistent with long-standing guidance, the Treasury Department and 
the IRS continue to agree with stakeholders that the plan of 
reorganization is relevant for determining the applicability of the 
definitional and operative provisions under subchapter C to 
dispositions of controlled corporation stock. Compare Rev. Rul. 2002-
85, 2002-2 C.B. 986 (concluding that an acquiring corporation's 
contribution of a target corporation's assets to a subsidiary 
corporation subsequent to a transaction otherwise qualifying as a 
reorganization under section 368(a)(1)(D) was ``pursuant to the plan of 
reorganization''; therefore, the continuity of business enterprise 
(COBE) requirement was not violated); Rev. Rul. 69-142, 1969-1 C.B. 107 
(concluding that an acquiring corporation's exchange of its debentures 
for those held by bondholders of the target corporation was not part of 
the reorganization exchange; therefore, the ``solely for voting stock'' 
requirement in section 368(a)(1)(B) was satisfied). In this regard, the 
``plan of reorganization'' concept provides a useful analogy for 
distinguishing distributions to which section 355 should apply from 
those to

[[Page 5234]]

which other sections of the Code (such as section 311) should apply.
    Accordingly, proposed Sec.  1.355-4 would set forth a series of 
provisions pursuant to which a taxpayer would establish its plan of 
distribution for distributions to which section 355(c) is purported to 
apply. These proposed rules generally would parallel the proposed plan 
of reorganization provisions in proposed Sec.  1.368-4, as discussed in 
more detail in part III.C of this Explanation of Provisions.
    Specifically, under the proposed rules, section 355 would apply to 
those distributions that are properly included in the plan of 
distribution and, therefore, are treated as ``part of the 
distribution'' within the meaning of section 355(a)(1)(D). Thus, for 
example, proposed Sec.  1.355-4(d)(2)(iii) would provide that 
distributions that are carried out in close temporal proximity with a 
section 355(c) distribution are not properly included in the plan of 
distribution and therefore would not qualify for nonrecognition 
treatment under section 355 unless Federal income tax principles 
(including the step transaction doctrine) would apply to determine that 
those distributions are in substance part of the plan of distribution 
for the section 355(c) distribution.
    Additionally, a distribution that is merely one of several (if not 
more) contemplated possibilities would not be properly included in the 
plan of distribution. Instead, proposed Sec.  1.355-4(d)(1) would 
require the distributing corporation to evidence a definite intent to 
carry out the distribution through a written commitment in one or more 
official records that substantiate the plan of distribution. As 
previously discussed in part I.B of this Explanation of Provisions, the 
Treasury Department and the IRS disagree with the stakeholders' view 
that a plan of distribution should reflect mere transactional 
possibilities under a ``wait and see'' approach. Adoption of this 
stakeholder recommendation would conflict with the requirement of 
section 355(a)(1)(D)(ii) that the non-tax avoidance nature of a 
retention be ``established to the satisfaction of the Secretary,'' 
because it would not be possible for the Secretary to establish the 
actual nature of a hypothetical transaction. In addition, adopting this 
stakeholder recommendation would both significantly compromise the 
IRS's ability to administer and enforce the requirements of section 355 
and reduce certainty regarding section 355 qualification.
    Under proposed Sec.  1.355-4(a)(2)(i) and (b)(1), the term ``plan 
of distribution'' generally would mean a plan of distribution 
established by a distributing corporation that satisfies all 
requirements set forth in proposed Sec.  1.355-4(c) and that is filed 
with the IRS pursuant to proposed Sec.  1.355-5. Proposed Sec.  1.355-
4(a)(2)(iii) and (b)(2) would provide that a plan of distribution also 
may be established based on corrections to the taxpayer-filed plan by 
the Commissioner based on all relevant facts and circumstances, all 
relevant provisions of the Code, and general principles of Federal 
income tax law (including the step transaction doctrine). If the 
taxpayer fails to file a plan of distribution under proposed Sec.  
1.355-5, proposed Sec.  1.355-4(a)(2)(iv) and (b)(2) would provide that 
the Commissioner may identify a plan of distribution for the 
transaction.
    Consistent with the objectives for guidance described in section 
2.01 of Notice 2024-38, the proposed plan of distribution provisions 
are intended to facilitate taxpayer certainty in identifying 
distributions to which section 355 properly should be applied. See, for 
example, proposed Sec.  1.355-4(c)(3)(i)(B) (providing a safe harbor 
presumption for timely prosecuting the plan of distribution) and (d) 
(providing rules for determining whether a distribution is properly 
included in the plan of distribution).
    In addition, the plan of distribution would provide the IRS with a 
single, timely document that identifies all relevant distributions 
necessary to determine the appropriate Federal income tax treatment of 
the purported section 355(c) distribution. This proposal, combined with 
the enhanced reporting requirements for section 355 transactions under 
proposed Sec.  1.355-5, would reestablish an appropriate line of sight 
for the IRS into taxpayer compliance under section 355, thereby helping 
to achieve the compliance and increased certainty objectives. Compare 
former Sec.  1.355-5 (effective from November 26, 1960, to May 29, 
2006) (requiring the taxpayer to ``attach to its return for the year of 
the distribution a detailed statement setting forth such data as may be 
appropriate in order to show compliance with the provisions of [section 
355]'').
5. Treatment of Delayed Distributions and Retentions
    The Treasury Department and the IRS appreciate the feedback 
received from stakeholders regarding the similarities between delayed 
distributions and retentions. The Treasury Department and the IRS agree 
with stakeholders that, because a section 355 transaction requires the 
distribution of controlled corporation stock by the distributing 
corporation, each of the following could apply to the same transaction: 
(i) the ``part of the distribution'' requirement in section 
355(a)(1)(D); (ii) the ``in pursuance of the plan of reorganization'' 
requirement in section 361; and (iii) the retention requirements in 
section 355(a)(1)(D)(ii).
    In particular, the Treasury Department and the IRS share the 
stakeholders' view that, if the distributing corporation does not 
distribute all its controlled corporation stock in the first 
distribution, the ``delayed distribution'' and ``retention'' labels 
give rise to a distinction without a difference in determining the 
existence of a genuine separation between the distributing corporation 
and the controlled corporation. In this respect, proposed Sec.  1.355-
2(e)(2)(iii) would focus on whether a genuine separation has occurred, 
without regard to whether the controlled corporation stock not 
distributed as part of the first distribution is disposed of through a 
distribution or transfer under section 361(c) or a taxable sale under 
section 1001.
    However, the Treasury Department and the IRS continue to view the 
``part of the distribution'' requirement in section 355(a)(1)(D), the 
``in pursuance of the plan of reorganization'' requirement in section 
361, and the ``no tax avoidance purpose'' requirement in section 
355(a)(1)(D)(ii) as discrete requirements that address discrete issues 
reflective of discrete policies. The ``part of the distribution'' 
requirement in section 355(a)(1)(D) serves as a scoping provision for 
the applicability of section 355(a)(1)(D)(i) and (ii) to distributions 
of controlled corporation stock. As discussed in parts I.C.4 and III.C 
of this Explanation of Provisions, the proposed plan of distribution 
and plan of reorganization rules would facilitate the determination of 
which distributions are ``part of the distribution.''
    As reflected in the legislative history of section 361, the ``in 
pursuance of the plan of reorganization'' requirement serves in large 
part to limit the application of the operative provisions in subchapter 
C to those transactions with a sufficiently proximate relationship with 
transactions that qualify under a definitional provision in subchapter 
C. See part II.A of the Background.
    Lastly, the ``no tax avoidance purpose'' requirement in section 
355(a)(1)(D)(ii) serves to ensure there is a genuine separation of the 
distributing corporation and the controlled corporation in situations 
in which the distributing corporation continues to

[[Page 5235]]

hold controlled corporation stock following the first distribution. 
This requirement applies regardless of whether that controlled 
corporation stock is disposed of pursuant to the plan of reorganization 
under section 361(c).
6. Timing Requirement for Control Distribution
    Consistent with the Supreme Court's decision in Gordon (discussed 
in part I.D.2 of the Background), proposed Sec.  1.355-2(e)(2) would 
require a distributing corporation, pursuant to a plan of distribution 
or plan of reorganization, as appropriate, to distribute an amount of 
stock of the controlled corporation constituting control (within the 
meaning of section 368(c)) either (i) within a single taxable year, or 
(ii) over two taxable years, but only if all distributions up to and 
including the control distribution are effectuated pursuant to a 
binding commitment that is described in the plan of distribution or 
plan of reorganization (as applicable). A two-year limitation for 
distributing control would provide taxpayers with additional 
transactional flexibility while facilitating the IRS's ability to 
administer and enforce the requirements of section 355. This approach 
would help achieve the increased certainty and transaction facilitation 
objectives of these proposed regulations.
7. Requirements for Nonrecognition Treatment
    In accordance with the foregoing discussion in this part I.C, these 
proposed regulations would revise Sec.  1.355-2(e) to provide that a 
distribution does not qualify for nonrecognition treatment under 
section 355(a)(1) unless the following requirements are satisfied. 
First, proposed Sec.  1.355-2(e)(2)(i) and (ii) would provide that the 
distributing corporation must distribute an amount of stock of the 
controlled corporation constituting control (within the meaning of 
section 368(c)) either (i) within a single taxable year, or (ii) during 
two taxable years, subject to the ``binding commitment'' requirement 
described in part I.C.6 of this Explanation of Provisions. Second, 
proposed Sec.  1.355-2(e)(2)(iii) would provide that any controlled 
corporation stock not distributed as part of the first distribution 
must satisfy the requirements for a qualifying retention in proposed 
Sec.  1.355-10(c).
    As previously discussed in parts I.C.1 through 3 of this 
Explanation of Provisions, to satisfy the requirements for a qualifying 
retention (and to thereby rebut the presumption of a tax avoidance 
purpose for the retention), the distributing corporation must: (i) 
either qualify for the section 355(a)(1)(D)(ii) safe harbor in proposed 
Sec.  1.355-10(c)(3) or satisfy the facts-and-circumstances test in 
proposed Sec.  1.355-10(c)(2)(ii); and (ii) vote any retained 
controlled corporation stock in proportion to votes cast by the 
controlled corporation's other shareholders (other than distributing 
corporation related persons). See proposed Sec.  1.355-10(c)(2)(iii).

II. Non-Substantive Modifications to Section 355 Regulations

    These proposed regulations would make certain non-substantive 
revisions to current Sec. Sec.  1.355-1 and 1.355-4. For example, these 
proposed regulations would modify current Sec.  1.355-1 by adding 
general definitions that apply for purposes of the section 355 
regulations, incorporating the rules in current Sec.  1.355-4 as 
proposed Sec.  1.355-1, and moving the applicability dates from current 
Sec.  1.355-1(a) to proposed Sec.  1.355-1(e). These revisions are not 
intended to make any substantive change.

III. Plan of Reorganization; Party to a Reorganization

A. Notice 2024-38

    As stated in section 2.02(4) of Notice 2024-38, the Treasury 
Department and the IRS understand that confusion and disagreement 
exists regarding the application of the ``plan of reorganization'' 
requirement to divisive reorganizations. For example, some stakeholders 
view the applicability of the ``plan of reorganization'' requirement to 
be potentially obviated by the temporal requirements set forth in 
section 3.04(6) of Rev. Proc. 2018-53 (concerning delayed satisfaction 
of distributing corporation debt). It is the view of the Treasury 
Department and the IRS that this is incorrect.
    Section 2.02(4) of Notice 2024-38 further states that, although the 
``plan of reorganization'' requirement incorporates a degree of 
transactional flexibility, such flexibility is limited by current 
Sec. Sec.  1.368-1(c) and 1.368-2(g), and the Treasury Department and 
the IRS view this requirement as helpful to ensure that delayed 
distributions are not used to avoid the repeal of the General Utilities 
doctrine (see part I.A.2 of the Background).

B. Stakeholder Input

    The Treasury Department and the IRS have received a broad spectrum 
of feedback from stakeholders regarding the ``plan of reorganization'' 
requirement. However, consistent with the view of the Treasury 
Department and the IRS set forth in Notice 2024-38, stakeholders 
uniformly have contended that this requirement should be applied in a 
flexible manner.
    Certain stakeholders have described the guidance in current Sec.  
1.368-2(g) regarding the meaning and scope of the ``plan of 
reorganization'' requirement as circular and incomplete. Those 
stakeholders similarly have described Sec.  1.368-1(c) as providing 
only conceptual guidance as to which transactions are properly included 
in a plan of reorganization. These stakeholders also have described 
Sec.  1.368-3(a) as requiring each party to the reorganization to adopt 
that plan but then failing to provide any guidance on how such parties 
are to satisfy that requirement. Stakeholders have aptly noted that 
Notice 2024-38 provided little additional clarity regarding the ``plan 
of reorganization'' requirement.
    Additionally, certain stakeholders have noted that few cases 
address the meaning and scope of the ``plan of reorganization'' 
concept, and that, even within such cases, courts often have applied 
the step transaction doctrine and the substance-over-form doctrine to 
determine the existence of a plan of reorganization. For example, one 
stakeholder highlighted King Enterprises, Inc. v. United States, 418 
F.2d 511 (Ct. Cl. 1969), in which the U.S. Court of Federal Claims 
applied the step transaction doctrine to treat the acquisition of stock 
of a target corporation (Tenco), followed by the merger of the target 
corporation into the acquiring corporation (Minute Maid), as a 
reorganization qualifying under section 368(a)(1)(A). The court 
identified the threshold issue as ``whether the transfer of Tenco stock 
to Minute Maid is to be treated for tax purposes as an independent 
transaction of sale, or as a transitory step in a transaction 
qualifying as a corporate reorganization,'' which dictated the 
resolution of the central issue of ``whether the initial exchange of 
stock was a step in a unified transaction pursuant to a `plan of 
reorganization'.'' King Enterprises, 418 F.2d at 514-15. Based on an 
analysis of the ``operative facts in this case,'' the court applied the 
step transaction doctrine to conclude that the two transactions 
comprised a single, unified transaction. Id. at 515-16, 519. Even 
though no formal plan of reorganization existed, the court relied on 
those facts and that analysis to identify a plan of reorganization for 
that unified transaction. Id. at 519 n.11 (relying on Redfield v. 
Commissioner, 34 B.T.A. 967 (1936), for the proposition

[[Page 5236]]

that ``[a] formal plan or reorganization is not necessary if the facts 
of the case show a plan to have existed'').
    In Seagram Corp. v. Commissioner, 104 T.C. 75 (1995), the Tax Court 
considered whether to integrate (i) an acquisition of stock of a target 
corporation (Conoco) through a first-step tender offer made by a 
subsidiary of an acquiring corporation (DuPont Tenderor and DuPont, 
respectively), and (ii) a subsequent merger of Conoco into DuPont 
Tenderor. The court acknowledged that the tender offer and subsequent 
merger each possessed independent significance, and that the subsequent 
merger was subject to several contingencies. Seagram, 104 T.C. at 93-
94. However, the court emphasized that DuPont and DuPont Tenderor 
``were under a binding and irrevocable commitment to complete the 
culminating merger--the second step--upon the successful completion of 
the DuPont tender offer--the first step.'' Id. at 98. Based on all 
facts and circumstances of the tender offer and subsequent merger, 
including official records of DuPont and DuPont Tenderor, the court 
identified the existence of a plan of reorganization, reasoning that, 
``because DuPont was contractually committed to undertake and complete 
the second-step merger once it had undertaken and completed the first-
step tender offer, these carefully integrated transactions together 
constituted a plan of reorganization within the contemplation of 
section 354(a).'' Id. at 98-99 (relying principally on, and noting 
satisfaction of, the Supreme Court's binding commitment standard in 
Gordon).
    Stakeholders also have noted that the Tax Court in Seagram 
characterized the ``plan of reorganization'' concept expressed in Sec.  
1.368-2(g) as one of ``substantial elasticity,'' relying on the court's 
prior observations on that concept in Int'l Telephone. Seagram, 104 
T.C. at 96. (In Int'l Telephone, the Tax Court noted that Sec.  1.368-
2(g) ``is imbued with qualities of flexibility and vagueness, with the 
result that it does not present precise self-executing guidelines.'' 77 
T.C. at 75.) The Tax Court in Seagram also relied on scholarly 
commentary for the proposition that, even though Sec.  1.368-2(g) at 
that time required a plan of reorganization to be filed with the IRS, 
it was self-evident that the IRS and the courts could identify the 
existence of a plan of reorganization in the event the taxpayer either 
did not file one or filed one that was inaccurate. See Seagram, 104 
T.C. at 96 (quoting Peter L. Faber, The Use and Misuse of the Plan of 
Reorganization Concept, 38 Tax L. Rev. 515, 523 (1982-1983)).
    Stakeholders also have commented on temporal considerations 
relating to plans of reorganization. Stakeholders have contended that 
the length of time between transactions effectuating a plan of 
reorganization should not prevent any particular transaction from being 
considered part of the plan. Conversely, these stakeholders have 
contended that the temporal proximity of one transaction to another 
transaction that is properly included in a plan of reorganization 
should not be determinative as to whether the other transaction is 
properly included in the plan. Stakeholders also have contended that 
imposing a time limitation for completing a plan of reorganization 
would be inappropriate.
    Additionally, some stakeholders have recommended granting taxpayers 
the flexibility to either execute the steps identified in the plan of 
reorganization or change them at any time, based on each taxpayer's 
judgment on how best to achieve the objectives of their transaction. 
However, other stakeholders have recommended clarifying that entering 
into a new transaction not contemplated by the plan, even in the 
alternative, is not treated as pursuant to the plan of reorganization.
    In sum, stakeholders uniformly have described the current 
regulations addressing the ``plan of reorganization'' requirement as 
lacking sufficient clarity and comprehensiveness. Accordingly, some 
stakeholders have requested guidance regarding the metrics needed for a 
taxpayer to establish a plan of reorganization. Specifically, 
stakeholders have requested guidance regarding (i) the means by which 
parties to a reorganization can adopt a plan of reorganization (in 
particular, some stakeholders have recommended allowing actions of a 
corporation's authorized representatives, and not just formal written 
actions of the board, to be taken into account for this purpose), (ii) 
transactions that may occur at a future time, are contingent, or are in 
the alternative, and (iii) transactions that may develop as a result of 
events arising after the plan of reorganization is adopted.
    The stakeholder input received has highlighted not only the 
deficiencies in authoritative guidance regarding the meaning and scope 
of the ``plan of reorganization'' requirement, but also the importance 
of this requirement in determining whether the operative provisions of 
subchapter C apply to a particular transaction.

C. Proposed Regulations

1. Overview
    The Treasury Department and the IRS agree with stakeholders that 
the current guidance regarding the ``plan of reorganization'' 
requirement is inadequate and creates significant confusion. Consistent 
with stakeholder recommendations, the proposed regulations would 
clarify, among other items, (i) the metrics needed for a taxpayer to 
establish a plan of reorganization, (ii) the manner whereby parties to 
a reorganization can adopt a plan of reorganization, and (iii) the 
requirements for prosecuting a plan of reorganization (including in the 
event of a change in circumstances following adoption of the plan). In 
proposing this guidance, the Treasury Department and the IRS have 
endeavored to balance the importance of providing taxpayers with 
transactional flexibility to effectuate bona fide business transactions 
with the need to facilitate IRS administration of the reorganization 
provisions of subchapter C. Accordingly, the Treasury Department and 
the IRS believe that this guidance would help achieve the compliance, 
increased certainty, and transaction facilitation objectives of these 
proposed regulations. (See the discussion of the objectives for 
guidance in part VI of the Background; see also the discussion of the 
TIGTA Report in part IV of the Background.)
2. Proposed Rules Regarding Plan of Reorganization
a. Purpose and Effect of Plan of Reorganization
    The Treasury Department and the IRS view a plan of reorganization 
as serving two related purposes. First, a plan of reorganization serves 
to identify those transactions to which the definitional and operative 
provisions of subchapter C apply. Second, a plan of reorganization 
serves to distinguish transactions the Federal income tax treatment of 
which is governed by the reorganization provisions of subchapter C from 
transactions to which the general recognition provisions of the Code 
(such as section 1001) apply.
    However, under the proposed regulations, a taxpayer's failure to 
set forth a plan of reorganization in a single, comprehensive document 
neither would be determinative as to the existence or scope of a plan 
of reorganization for a transaction nor would govern the application of 
any definitional or operative provision to that transaction. See 
proposed Sec.  1.368-4(a)(3).

[[Page 5237]]

b. Determination of Plan of Reorganization
    The proposed regulations would permit a plan of reorganization to 
be determined in several different manners. Under the manner preferred 
by the Treasury Department and the IRS, a taxpayer would prepare a 
single, comprehensive document that satisfies all requirements set 
forth in proposed Sec.  1.368-4(d) and file that document with the IRS 
as required by proposed Sec.  1.368-3(a)(5) (taxpayer-filed plan of 
reorganization). See proposed Sec.  1.368-4(b)(1). The taxpayer-filed 
plan of reorganization would contain the information required by prior 
and current Sec.  1.368-3(a) and incorporate recommendations of the 
TIGTA Report.
    Specifically, proposed Sec.  1.368-4(d) would set forth the 
following requirements. First, the proposal would require the taxpayer-
filed plan of reorganization to identify (i) all parties to the 
reorganization (as required by current Sec.  1.368-3(a)), (ii) all 
transactions properly included in the plan of reorganization (as 
required by prior Sec.  1.368-3(a)), and (iii) all liabilities 
(including debt) to be assumed by the acquiring corporation and the 
obligees (or creditors) of those liabilities, and (iv) all debt of the 
target corporation that will be satisfied with section 361 
consideration and the creditors of that debt. Second, the proposal 
would require such plan to describe the intended Federal income tax 
treatment of those transactions (which would facilitate implementing 
the recommendations of the TIGTA Report). Third, the proposal would 
require such plan to describe the corporate business purpose for each 
transaction (consistent with current Sec.  1.368-2(g)). Lastly, the 
proposal would require such plan to establish that each transaction 
facilitates the continuance of the business of a corporation a party to 
the reorganization (consistent with current Sec.  1.368-2(g)). See 
proposed Sec.  1.368-4(d)(1).
    The proposed regulations would reflect a preference that taxpayers 
will timely file a complete and accurate plan of reorganization. See 
proposed Sec.  1.368-4(c)(1). Accordingly, the Federal income tax 
consequences of the subject transactions generally would be determined 
in accordance with that plan. See proposed Sec.  1.368-4(a)(2)(i). 
Throughout the duration of the transaction or series of transactions, 
which potentially could span several taxable years, the IRS would 
possess the ability to monitor the taxpayer's execution of that plan of 
reorganization (for example, through the taxpayer's annual filing of 
Form 7216 for divisive transactions). The Treasury Department and the 
IRS intend the proposed approach (i) to increase taxpayer certainty 
regarding the Federal income tax treatment of transactions properly 
included in a plan of reorganization, and (ii) to facilitate IRS 
administration of the reorganization provisions of subchapter C.
    However, if a taxpayer files a plan of reorganization with the IRS 
that fails to satisfy any requirement set forth in proposed Sec.  
1.368-4(d), or if the taxpayer fails to file a plan of reorganization 
with the IRS in accordance with proposed Sec.  1.368-3(a)(5), proposed 
Sec.  1.368-4(c)(2)(i) recognizes that the Commissioner may correct or 
identify a plan of reorganization. Under proposed Sec.  1.368-
4(c)(2)(ii), the Commissioner may determine that a transaction or 
series of transactions should be included in, or excluded from, a plan 
of reorganization based on (i) all facts and circumstances regarding 
the transaction or series of transactions, and (ii) all relevant 
provisions of the Code and general principles of Federal income tax 
law, including the step transaction doctrine.
    The proposed approach is consistent with long-standing caselaw 
indicating that the existence and proper scope of a plan of 
reorganization can be determined in the absence of formal 
documentation. See, for example, Redfield, 34 B.T.A. at 973 (``It is 
not necessary, however, that such a plan of reorganization be evidenced 
by a formal written document, such as a contract or corporate minutes. 
It is sufficient if the circumstances indicate that the various steps 
taken were pursuant to a definite plan of reorganization.''); Fry v. 
Comm'r, 5 T.C. 1058, 1070 (1945) (similar). The proposed regulations 
would reflect this long-standing position because conditioning the 
applicability of the definitional and operative provisions of 
subchapter C on whether a plan of reorganization formally was prepared 
and filed would, in particular and contrary to law, make the 
reorganization regime entirely elective.
    Nonetheless, the Treasury Department and the IRS are of the view 
that formal documentation requirements for taxpayer-filed plans of 
reorganization are necessary to facilitate the IRS's administration of 
the reorganization provisions of subchapter C. See part III of the 
Background. Moreover, the preference for complete and accurate 
taxpayer-filed plans of reorganization under proposed Sec.  1.368-
4(c)(1) requires adequate substantiation with the IRS, which would be 
provided by objectively verifiable, official corporate documents. 
Accordingly, proposed Sec.  1.368-4(d) would enhance the current 
reporting requirements for plans of reorganization.
c. Agreement by Parties to Plan of Reorganization; Beginning of Plan of 
Reorganization
    Proposed Sec.  1.368-4(d)(2) would provide that, prior to the first 
step of a reorganization, the plan of reorganization or an original 
plan of reorganization that becomes the amended plan of reorganization, 
as applicable, must be finalized and adopted by the party to the 
reorganization. Taxpayers would demonstrate satisfaction of this 
requirement through (i) the acts of duly authorized officers and 
directors of the corporation, and (ii) the official records of the 
party to the reorganization.
    The Treasury Department and the IRS are of the view that the 
proposed approach would provide greater taxpayer certainty regarding 
the means by which parties to a reorganization can adopt a plan of 
reorganization than current Sec.  1.368-3(a), which provides only that 
``[t]he plan of reorganization must be adopted by each of the 
corporations that are parties thereto.'' As previously discussed in 
part III.B of this Explanation of Provisions, the current regulations 
have created significant uncertainty due to the lack of guidance on 
what constitutes an ``adoption'' by the parties. The proposed 
regulations would address this uncertainty in a manner consistent with 
prior Sec.  1.368-3(a) and statutory law. See section 806(g)(3) of the 
Tax Reform Act of 1976 (Public Law 94-455, 90 Stat. 1520, 1606) 
(describing how a corporation is considered to have adopted a plan of 
reorganization for purposes of determining the effective date of 
certain modifications to sections 382 and 383).
    In addition, the proposed substantiation requirements would 
facilitate the IRS's administrative function by marking the beginning 
of the taxpayer's plan of reorganization--a feature that the Tax Court 
also views as important. See Seagram, 104 T.C. at 98 (emphasizing in 
its plan of reorganization analysis that the DuPont/Conoco Agreement 
``provides a discrete start and finish'').
d. Timing Requirement for Completion of Plan of Reorganization
i. General ``Expeditious Completion'' Requirement
    Proposed Sec.  1.368-4(d)(3)(i)(A) and (ii)(A) would require that, 
taking into account all facts and circumstances (including the one or 
more corporate

[[Page 5238]]

business purposes for a reorganization), all parties to the 
reorganization must complete the plan of reorganization as 
expeditiously as practicable, and in the manner described in that plan. 
The proposed approach takes into account taxpayers' need for 
transactional flexibility and reflects the long-standing principle that 
the passage of time is not determinative of whether a transaction is 
part of a plan of reorganization. See, for example, Wilson v. Comm'r, 
T.C. Memo. 1961-135 (``The mere lapse of time is not decisive. The 
important thing is that the steps which are taken evidence a consistent 
performance of the reorganization plan and purpose.'').
ii. Presumption of Satisfaction if Completion Within 24 Months
    However, the Treasury Department and the IRS are concerned that the 
lack of a time limitation for completing a plan of reorganization 
raises administrability concerns for the IRS. Accordingly, the Treasury 
Department and the IRS are (i) issuing proposed Sec.  1.355-5, and (ii) 
introducing new Form 7216, to provide the IRS with information 
regarding divisive transactions that span multiple tax years. See part 
V of the Background.
    Additionally, temporal guidelines would provide greater certainty 
to taxpayers. In this regard, stakeholders have requested the inclusion 
of safe harbors in these proposed regulations to mitigate uncertainty 
arising from conceptual rules and facts-and-circumstances 
determinations. Based on this feedback, proposed Sec.  1.368-
4(d)(3)(i)(B) would provide that the ``expeditious completion'' 
requirement is presumed to be satisfied if all parties to a 
reorganization complete the plan of reorganization within the 24-month 
period beginning on the date of the first step of the plan of 
reorganization. This increased certainty would help achieve the 
transaction facilitation objective of these proposed regulations, and 
providing a 24-month safe harbor would help achieve the compliance 
objective of these proposed regulations.
e. Requirements for Transactions To Be Treated as Properly Included in 
Plan of Reorganization
i. Overview
    Stakeholders have recommended various standards and approaches for 
determining whether a transaction is properly included in a plan of 
reorganization. As noted by stakeholders, neither current guidance nor 
the caselaw regarding the ``plan of reorganization'' requirement 
adequately addresses this issue. The proposed regulations would 
synthesize the overarching principles of this caselaw into rules that 
could be applied by taxpayers and the IRS with significantly greater 
certainty than under current Treasury guidance and the caselaw.
ii. Definite Intent Requirement
    As a threshold requirement, proposed Sec.  1.368-4(e)(1)(i) would 
require that, prior to the first step of a plan of reorganization or an 
original plan of reorganization that becomes the amended plan of 
reorganization, one or more parties to the reorganization must evidence 
a definite intent to carry out the transaction. This definite intent 
must be evidenced through a written commitment in one or more official 
records of the party that substantiate the plan of reorganization. 
Under this proposal, the existence of contingencies or conditions would 
not be conclusive in determining whether a party to the reorganization 
satisfies this requirement.
    The ``definite intent'' standard is intended to provide sufficient 
transactional flexibility to encourage bona fide business transactions 
in a manner consistent with long-standing caselaw. The origins of the 
``definite intent'' standard can be traced back to judicial opinions of 
the Board of Tax Appeals (BTA), the predecessor to the Tax Court. For 
example, in Fry v. Commissioner, the BTA relied on this standard for 
determining the existence of a plan of reorganization from ``what 
appear[ed] on the minutes of the meeting of the stockholders and the 
meeting of the board of directors of the old bank,'' which had 
articulated the business objectives and transaction steps for the 
reorganization. 5 T.C. at 1070; see also Redfield, 34 B.T.A. at 973 
(noting that, although a formal written plan of reorganization is not 
necessary, the circumstances evidencing that a reorganization occurred 
need to indicate that the various steps taken in pursuance thereof were 
taken ``pursuant to a definite plan of reorganization'') (emphasis 
added); Seagram, 104 T.C. at 97 (observing that the DuPont/Conoco 
Agreement ``definitively states the terms for `the acquisition of 
[Conoco] by [DuPont Tenderor and]' sets out . . . the series of 
transactions which in their totality were intended to accomplish a 
section 368 reorganization'').
    In contrast, courts have determined that transactions subject to a 
lesser degree of intent or predominated by uncertainty are not properly 
included in a plan of reorganization. For example, in National Bank of 
Commerce in Memphis v. United States, 87 F. Supp. 302 (W.D. Tenn. 
1949), the court concluded that a transaction contemplated prior to the 
plan of reorganization was not properly included in that plan because 
the transaction was uncertain and indefinite as of the time of the 
first step of the plan of reorganization. 87 F. Supp. at 304. The court 
emphasized that ``[a]n element in a plan of reorganization that cannot 
be legally enforced and, in addition is fraught with much uncertainty, 
is indefinite and not necessary to the reorganization, cannot be 
considered as one of the steps resulting in the completed 
transaction.'' Id. Accordingly, if the parties did not anticipate or 
otherwise contemplate a transaction prior to the adoption of the plan 
of reorganization, that transaction cannot be included in that plan. 
See Atwood Grain & Supply Co. v. Comm'r, 60 T.C. 412, 423 (1973) 
(observing that ``[t]here [wa]s no evidence that issuance of the 
preferred stock was contemplated either in the merger negotiations or 
in the merger agreement,'' and reasoning that, ``[i]n order to include 
events occurring after a merger in the plan of merger there must be 
some anticipation of the event in the merger'').
    Stakeholders have noted that a ``plan of reorganization'' concept 
that includes every possibility considered by any taxpayer in 
connection with a reorganization would be overbroad and meaningless. 
Indeed, a commenter relied upon by the Tax Court for its analysis in 
Seagram noted that ``[t]he contemplated possibility standard is too 
broad. . . . A more appropriate standard would be to link the later 
transaction to the earlier one only if there is a firm commitment to 
consummate it.'' Faber, The Use and Misuse of the Plan of 
Reorganization Concept, 38 Tax L. Rev. at 547. The Treasury Department 
and the IRS agree that such a standard would not be appropriate for the 
proposed regulations. Accordingly, proposed Sec.  1.368-4(e)(1)(iii)(A) 
would provide that mere contemplation that a transaction may be carried 
out would not be sufficient to satisfy the ``definite intent'' 
requirement, regardless of whether that contemplated transaction is 
included in an official record of the party.
    However, the Treasury Department and the IRS recognize that the 
``contemplated possibility'' standard is relevant for certain plan of 
reorganization determinations. Accordingly, proposed Sec.  1.368-
4(e)(1)(iii)(B) would provide that a party's mere contemplation of a 
transaction may be relevant for purposes of the correction or 
identification of a plan of reorganization by the

[[Page 5239]]

Commissioner. As previously discussed in part III.C.2.b. of this 
Explanation of Provisions, the Commissioner's determination under 
proposed Sec.  1.368-4(c)(2)(ii) would be based on all facts and 
circumstances pertaining to the transaction and the application of all 
relevant Code provisions and Federal income tax principles, including 
the step transaction doctrine.
    Permitting the IRS to determine the outer reaches of the scope of 
transactions potentially includable in a plan of reorganization through 
an analysis of all facts and circumstances and Federal income tax 
principles would be consistent with judicial authorities that have 
applied a ``contemplated possibility'' test. For example, in Anheuser-
Busch, Inc. v. Commissioner, 40 B.T.A. 1100 (1939), the BTA relied on 
substance-over-form principles to determine the scope of transactions 
included in a plan of reorganization, based on its determination that a 
first-step transfer to a parent corporation was ``transitory and 
without real substance.'' 40 B.T.A. at 1106. As part of its analysis, 
the court observed that the parent had ``contemplated,'' but was not 
obligated to carry out, the immediate transfer of the property received 
to its subsidiary, and the court expanded the scope of the plan of 
reorganization to include that second-step transfer. Id. at 1106-07 
(relying on the substance-over-form analysis of Helvering v. Bashford, 
302 U.S. 454, 458 (1938)). Other judicial opinions similarly have used 
the existence of a contemplated possibility in this manner. See, for 
example, Avco Mfg. Corp. v. Comm'r, 25 T.C. 975, 984-85 (1956) (noting 
that a ``subsequent transfer of the property . . . was a contemplated 
possibility under the plan that actually eventuated'' and was properly 
included within the scope of the plan of reorganization under the 
mutual interdependence test); Transport Products Corp. v. Comm'r, 25 
T.C. 853, 857-58 (1956).
    Once a definite intent is established, the existence of 
contingencies and other conditions that could affect prosecution of the 
plan of reorganization are not treated as diminishing that level of 
intent. See, for example, Seagram, 104 T.C. at 96 (``DuPont had an 
indisputable legal obligation to complete the Merger with Conoco, 
notwithstanding the possibility of intervening legal impediments, or 
contingencies, which in fact, never materialized''). Accordingly, 
proposed Sec.  1.368-4(e) would provide that, for purposes of 
determining whether a party to a reorganization satisfies the 
``definite intent'' requirement, the existence of contingencies or 
conditions is not conclusive.
    Section 355 transactions would be subject to a special definite 
intent requirement under proposed Sec. Sec.  1.355-4(d)(1)(ii) and 
1.368-4(e)(1)(ii). Specifically, if a control distribution occurs in a 
later taxable year than the first distribution, the distributing 
corporation would not be treated as establishing a definite intent 
unless all distributions up to and including the control distribution 
are effectuated pursuant to a binding commitment. This proposed special 
``definite intent'' requirement would reflect the Supreme Court's 
decision in Gordon. See also the discussion in part I.D.2 of the 
Background.
iii. Proximate Relationship Requirement
(a) Overview
    The proposed regulations would set forth standards for determining 
whether a transaction shares a sufficient relationship with other 
transactions to which a definitional or operative provision applies. To 
reflect the distinct purposes for, and requirements of, the 
definitional provisions and the operative provisions in subchapter C, 
the proposed regulations would set forth two different sets of 
proximate relationship requirements.
(b) Necessary or Integral Test for Qualification Under Definitional 
Provisions
    Under proposed Sec.  1.368-4(e)(2)(i)(A), a transaction would be 
treated as part of the plan of reorganization for a reorganization to 
which a definitional provision can apply only if, on its own or as part 
of a series of transactions, the transaction either (i) is necessary to 
satisfy one or more requirements of the definitional provision, or (ii) 
is an integral part of a series of transactions carried out to satisfy 
the requirements of the definitional provision. In practice, the 
``integral part'' test generally would be relevant for transactions 
that are not ``necessary to satisfy'' one or more requirements of a 
definitional provision. The proposed regulations would require 
satisfaction of either condition to be evidenced by a written 
commitment in one or more official records of the party to the 
reorganization. See proposed Sec.  1.368-4(e)(2)(i)(A).
    The ``necessary to satisfy'' condition is intended to convey, with 
more precision, a requirement set forth in current Sec.  1.368-2(g). 
Section 1.368-2(g) states, in part, that ``[t]he term plan of 
reorganization has reference to a consummated transaction specifically 
defined as a reorganization under section 368(a).'' In addition, 
current Sec.  1.368-2(g) provides that ``[t]he term is not to be 
construed as broadening the definition of `reorganization' as set forth 
in section 368(a).'' The Treasury Department and the IRS view the 
``necessary to satisfy'' condition as already clear (given that the 
definitional provisions in section 368(a)(1) describe the steps 
necessary for qualification) but have rearticulated this standard to 
eliminate the circularity and vagueness that courts and stakeholders 
have identified in current Sec.  1.368-2(g). See Int'l Telephone, 77 
T.C. at 75 (noting such vagueness); Seagram, 104 T.C. at 96 
(highlighting the Tax Court's observation in Int'l Telephone).
    The ``integral part'' condition also is embedded in current Sec.  
1.368-2(g), which provides that the term ``plan of reorganization'' is 
to be taken as limiting the nonrecognition of gain or loss to ``such 
exchanges or distributions as are directly a part of the transaction 
specifically described as a reorganization in section 368(a)'' 
(emphasis added). The Treasury Department and the IRS view this 
``directly a part'' standard as less stringent than the ``necessary to 
satisfy'' standard but nonetheless view it as mandating that a 
transaction must be essential to qualifying a series of transactions as 
a reorganization. Accordingly, the proposed regulations would replace 
the phrase ``directly a part of the transaction'' with an ``integral 
part'' standard.
    The proposed ``integral part'' standard is intended to reflect the 
structure of section 368(a)(1) and the long-standing position of the 
IRS and the courts. For example, a distributing corporation that 
retains controlled corporation stock may qualify under section 355--and 
therefore ultimately may satisfy a condition in section 368(a)(1)(D)--
through multiple types of dispositions of controlled corporation stock. 
In each instance, such disposition may be viewed as integral to section 
368(a)(1)(D) qualification. (See also the requirements for qualifying 
retentions previously discussed in part I.C of this Explanation of 
Provisions.)
    The foregoing principle is reflected in Rev. Rul. 57-518, 1957-2 
C.B. 253, which addressed whether a transaction satisfied a prior 
version of section 368(a)(1)(C) that did not yet impose a liquidation 
requirement. In Rev. Rul. 57-518, a target corporation transferred 70 
percent of its assets to an acquiring corporation for acquiring 
corporation voting stock. The target corporation then disposed of all 
its remaining assets in recognition transactions (that is, not under 
the operative nonrecognition

[[Page 5240]]

provisions of subchapter C) and liquidated. Although the liquidation 
was not described in, or required by, that prior version of section 
368(a)(1)(C), the IRS concluded that the liquidation was part of the 
plan of reorganization. Like the disposition by a distributing 
corporation of retained controlled corporation stock in a transaction 
to which section 1001 applies, the target corporation liquidation was 
not necessary to achieve qualification under section 368(a)(1), but it 
was an integral part of a series of transactions carried out to satisfy 
the requirements of that definitional provision.
(c) But for, or Integral to, Test for Application of Operative 
Provision
    Under proposed Sec.  1.368-4(e)(2)(i)(B), a transaction would be 
treated as part of the plan of reorganization to which an operative 
provision can apply only if, on its own or as part of a series of 
transactions, the transaction either (i) would not have occurred but 
for the reorganization that is covered by the plan of reorganization, 
or (ii) is an integral part of a series of transactions carried out to 
satisfy the requirements of the definitional provision intended to 
apply to the reorganization. The proposed regulations would require 
satisfaction of either condition to be evidenced by a written 
commitment in one or more official records of the party to the 
reorganization. Both of these conditions are intended to replace the 
``directly a part of'' standard set forth in current Sec.  1.368-2(g) 
with standards that are clearer and more reflective of the purpose and 
requirements of the operative provisions in subchapter C.
    The proposed ``but for'' condition is embedded within the 
``directly a part of'' requirement in current Sec.  1.368-2(g). Among 
other objectives, this proposed condition is intended to help clarify 
the determination of whether an operative provision applies to a 
distribution that occurs within close temporal proximity to one or more 
transactions that are properly included in a plan of reorganization. 
For example, in determining whether section 361(b) should apply to a 
distribution by a distributing corporation to its shareholders in close 
temporal proximity to a divisive reorganization, the proposed ``but 
for'' test would clarify that section 361(b) treatment would be 
applicable only if that distribution would not have occurred ``but 
for'' the divisive reorganization. See the examples in proposed Sec.  
1.361-3(f)(2) through (5).
    An ``integral part'' standard also would increase taxpayer 
certainty as compared to the current ``directly a part of'' standard, 
particularly because courts historically have applied an ``integral 
part'' standard. For example, in Sheldon v. Commissioner, 6 T.C. 510 
(1946), the Tax Court found that a transaction was integral to a merger 
even though the transaction was not necessary for qualification for a 
definitional provision under section 368(a)(1). In Sheldon, the Tax 
Court considered whether a pre-merger distribution should be included 
in the plan of reorganization for the merger. 6 T.C. at 517-18. The 
court emphasized that the pre-merger distribution was made to equalize 
values of the target corporation and the acquiring corporation so that 
the merger could be one of equals, thereby satisfying a condition for 
executing the merger. Id. In its analysis, the court provided that 
``[t]he purpose of this distribution, its place in the sequence of 
events, and the surrounding circumstances, lead to but one conclusion. 
They all demonstrate that it was an integral part of the reorganization 
transaction as a whole and must be treated in connection with it.'' Id. 
at 517. See also Int'l Telephone, 77 T.C. at 76 (noting the absence of 
``a binding agreement or other factors indicating that conversion [of 
debentures] was an integral part of the plans of reorganization'').
    Additionally, the Treasury Department and the IRS are of the view 
that replacing the ``directly a part of'' standard in current Sec.  
1.368-2(g) with the standards in proposed Sec.  1.368-4(e)(2)(i)(B) 
would improve taxpayer certainty in determining the applicability of an 
operative provision of subchapter C. Proposed Sec.  1.368-4(e) would 
provide additional certainty by requiring the ``but for'' standard to 
be applied in tandem with the ``definite intent'' requirement set forth 
in proposed Sec.  1.368-4(e)(1). In other words, a transaction would 
not be properly included in a plan of reorganization if the party to 
the reorganization failed to evidence a definite intent to carry out 
that transaction, regardless of whether the transaction would not have 
occurred ``but for'' the reorganization.
    This implementation of the ``but for'' standard would be consistent 
with judicial authorities, including those cited by stakeholders. For 
example, in International Telephone, the Tax Court considered exchanges 
involving debentures that could not have occurred but for the execution 
of a reorganization that qualified under section 368(a)(1)(C). 77 T.C. 
at 72-78. Although the court observed the existence of that ``but for'' 
relationship, the court reasoned that ``[t]he fact that [the acquiring 
corporation] assumed the conversion obligation as part of the plans of 
reorganization does not mean . . . that the subsequent conversions and 
retirement of the debentures were also part of the reorganizations.'' 
Id. at 76. Based on the lack of indicia indicating satisfaction of the 
proposed ``direct intent'' requirement, the Tax Court concluded that 
such exchanges were not properly included in the plan of 
reorganization. See id. at 76-77 (noting the lack of any binding 
agreement, any other type of obligation, or other facts that would 
indicate satisfaction of the ``direct intent'' requirement). See also 
Becher v. Comm'r, 22 T.C. 932 (1954) (treating a distribution as not 
part of the plan of reorganization under the predecessor to section 
368(a)(1)(D), and therefore not ``boot,'' based on an examination of 
the facts and circumstances of the distribution and the transactions 
comprising the reorganization).
(d) Independent Legal Significance; Temporal Proximity
    Proposed Sec.  1.368-4(e)(2)(ii) would confirm that the independent 
significance of a transaction (for example, the fact that the 
transaction has a separate business motive apart from the 
reorganization) does not preclude satisfaction of the proximate 
relationship requirements in proposed Sec.  1.368-4(e)(2)(i)(A) and 
(B). The Treasury Department and the IRS view this approach as 
consistent with established caselaw (see Seagram, 104 T.C. at 91-93) 
and reflective of the realities of bona fide business transactions. It 
has long been the understanding of the Treasury Department and the IRS 
that a transaction could be included in the plan of reorganization even 
though it may have separate business motives, or separate and permanent 
legal, economic, and business consequences, apart from the 
reorganization.
    Additionally, proposed Sec.  1.368-4(e)(2)(iii) would provide that 
a transaction occurring in close temporal proximity to one or more 
other transactions is not properly included in a plan of reorganization 
unless Federal income tax principles (including the step transaction 
doctrine) would apply to determine that the transaction was, in 
substance, part of the plan of reorganization.
iv. Business Purpose Consistency Requirement
    Lastly, in order for a transaction to be treated as properly 
included in a plan of reorganization, proposed Sec.  1.368-4(e)(3) 
would require the transaction (on its

[[Page 5241]]

own, or as part of a series of transactions) to be consistent with, and 
directly related to, one or more corporate business purposes for the 
reorganization (for example, the transaction directly furthers one or 
more corporate business purposes for the reorganization).
    The Treasury Department and the IRS view the proposed corporate 
business purpose consistency requirement as reflective of established 
caselaw. See Seagram, 104 T.C. at 83, 97 (noting that the tender offer 
and the merger shared the same corporate business purpose of enabling 
DuPont to acquire all the stock of Conoco). In addition, the Treasury 
Department and the IRS view this proposed rule as conceptually grounded 
in current Sec.  1.368-2(g), which provides that ``the readjustments 
involved in the exchanges or distributions effected in the consummation 
[of the reorganization] must be undertaken for reasons germane to the 
continuance of the business of a corporation a party to the 
reorganization.''
f. Amended Plan of Reorganization
    The Treasury Department and the IRS recognize that, in certain 
circumstances, taxpayers may need to amend their plans of 
reorganization. Accordingly, proposed Sec.  1.368-4(f)(1) would provide 
that, if a taxpayer amends a plan of reorganization after the first 
step of the original plan (amended plan of reorganization), those 
amendments do not cause the taxpayer to fail to satisfy the ``plan of 
reorganization'' requirements set forth in proposed Sec.  1.368-4(d) 
only if the following requirements are satisfied. First, the amendments 
to the plan must be in direct response to an identifiable, unexpected, 
and material change in market or business conditions that occurs after 
the date on which the original plan of reorganization is adopted by the 
party to the reorganization. Second, the amendments must be necessary 
to effectuate the reorganization. Third, the amended plan of 
reorganization must satisfy all requirements set forth in proposed 
Sec.  1.368-4(d) to qualify as a plan of reorganization.
    If the taxpayer satisfies the requirements in proposed Sec.  1.368-
4(f)(1), proposed Sec.  1.368-4(f)(2)(i) would provide that the 
definitional and operative provisions described in proposed Sec.  
1.368-1(c)(2)(i) and (ii) would apply to the transactions identified 
in, and carried out pursuant to, the amended plan of reorganization. In 
other words, the proposed regulations would confirm that the Federal 
income tax consequences of all transactions properly included in the 
amended plan of reorganization would be determined based on that plan 
of reorganization (and not on the original plan of reorganization). 
However, proposed Sec.  1.368-4(f)(2)(ii) would provide that, if the 
amended plan of reorganization fails to satisfy the requirements in 
proposed Sec.  1.368-4(f)(1), the Commissioner may correct or identify 
the amended plan of reorganization.
3. Proposed Rules Regarding Party to a Reorganization
    In addition to providing rules regarding the determination, 
adoption, and prosecution of a plan of reorganization, the proposed 
regulations would revise current Sec.  1.368-2(f) to further clarify 
(i) which persons are parties to a reorganization, and (ii) the 
consequences of determining that a person is (or is not) a party to a 
reorganization.
    Proposed Sec.  1.368-2(f)(1) generally would provide that the 
definitional and operative provisions described in Sec.  1.368-
1(c)(2)(i) and (ii), respectively, apply solely to a transaction that 
is carried out by, between, or among one or more parties to a 
reorganization. For purposes of determining the scope of transactions 
to which those provisions apply, the term ``party to a reorganization'' 
would be limited under proposed Sec.  1.368-2(f)(2) through (4) solely 
to a corporation that (i) engages in a transaction or series of 
transactions that satisfies a definitional provision set forth in 
section 368(a)(1), and (ii) is determined to be a party to a 
reorganization, as further described in the following paragraph.
    In general, proposed Sec.  1.368-2(f)(4)(i) would provide that a 
corporation's status as a party to a reorganization is established 
solely by the inclusion and identification of the corporation as a 
party to the reorganization in a plan of reorganization filed with the 
IRS pursuant to proposed Sec.  1.368-3(a)(5). However, proposed Sec.  
1.368-2(f)(4)(ii) would provide that the corporation's status as a 
party to a reorganization may be determined by the Commissioner based 
on (i) all facts and circumstances regarding the transaction or series 
of transactions, and (ii) all relevant provisions of the Code and 
general principles of tax law, including the step transaction doctrine.
    Proposed Sec.  1.368-2(f)(3)(ii) would retain the rules in current 
Sec.  1.368-2(f) regarding the impact of certain transfers of assets or 
stock in a reorganization on a person's status as a party to the 
reorganization.

IV. Application of Substance-Over-Form, Agency, and Other Relevant 
Theories to Intermediated Exchanges and Direct Issuance Transactions

A. Notice 2024-38

    In section 2.02(5) of Notice 2024-38, the Treasury Department and 
the IRS announced that they are continuing to study the application of 
the Code, as well as general principles of Federal income tax law 
(including substance-over-form, agency, or other relevant theories), to 
monetization transactions involving section 361 consideration. In 
particular, this study continues to focus on intermediated exchanges, 
which occur through (i) the acquisition by an intermediary (such as an 
investment bank) of historical distributing corporation debt from 
holders of that debt, and (ii) the subsequent satisfaction of that debt 
by the distributing corporation using section 361 consideration.
    As capital market transactions have evolved, this study also has 
focused increasingly on direct issuance transactions, which typically 
occur through: (i) the issuance of new debt by a distributing 
corporation to an intermediary for cash in anticipation of a divisive 
reorganization; (ii) the use of that cash by the distributing 
corporation to satisfy historical distributing corporation debt, during 
a potentially indefinite period; and (iii) the satisfaction of that new 
debt by the distributing corporation through the transfer of section 
361 consideration to the intermediary.
    This study reflects the long-standing position of the Treasury 
Department and the IRS that general principles of Federal income tax 
law (including substance-over-form, agency, or other relevant theories) 
apply to determine the Federal income tax consequences of all 
transactions, including such monetization transactions. See United 
States v. Fruehauf Corp., 577 F.2d 1038, 1068 (6th Cir. 1978) (``The 
incidence of federal taxation has always depended upon the substance of 
transactions . . .''). Indeed, this position is consistent with nearly 
a century of Supreme Court precedent beginning with the Court's 
decision in Gregory v. Helvering, which established that the 
application of the Code to a transaction (or series of transactions) 
turns on the substance of the transaction. See Gregory, 293 U.S. at 
467-70 (concluding that the ``reorganization attempted was without 
substance and must be disregarded [and] [t]o hold otherwise would be to 
exalt artifice above reality and to deprive the statutory provision in 
question of all serious purpose'');

[[Page 5242]]

United States v. Iles, 906 F.2d 1122, 1127 (6th Cir. 1990) (``The 
Supreme Court has recognized, at least as far back as Gregory v. 
Helvering . . . that substance over form governs federal taxation.'') 
(citations omitted).
    The application of substance-over-form and similar doctrines can 
affect qualification for nonrecognition treatment under section 361. 
Notice 2024-38 conveyed the long-standing view of the Treasury 
Department and the IRS that the application of agency principles to an 
intermediated exchange involving so-called ``old and cold'' 
distributing corporation debt could cause that transaction to be 
recharacterized for Federal income tax purposes such that the 
distributing corporation would not be treated as transferring section 
361 consideration to a creditor in satisfaction of distributing 
corporation debt. In other words, if the intermediary were found to be 
acting on behalf of the distributing corporation under agency 
principles, transfers of section 361 consideration to the intermediary 
would not satisfy the requirements for nonrecognition under section 
361. With respect to a direct issuance transaction in which the 
distributing corporation issues and redeems the new debt in close 
temporal proximity, the Treasury Department and the IRS are of the view 
that the transaction could be recast under general principles of 
Federal income tax law such that the nonrecognition requirements under 
section 361 are not satisfied.

B. Stakeholder Input

1. Intermediated Exchanges
    Stakeholders have contended that intermediated exchanges should not 
be subject to recharacterization, provided that the distributing 
corporation establishes the intermediary's status as a creditor acting 
for its own account under agency principles. Stakeholders have stated 
that this approach would be consistent with Rev. Rul. 2017-9, 2017-21 
I.R.B. 1244, because intermediated exchanges (i) do not conflict with 
the underlying policy of section 361(c)(3), (ii) do not avoid the 
result intended by section 361(c)(3) (that is, the reallocation of 
historical distributing corporation liabilities to the controlled 
corporation), and (iii) do not produce results that are inconsistent 
with the underlying intent of section 361(c)(3). In other words, 
stakeholders have suggested that, in determining whether an 
intermediated exchange should be recharacterized, the relevant question 
is whether the distributing corporation debt acquired by the 
intermediary was issued with a purpose of avoiding any requirement or 
limitation under section 361.
    In this regard, one stakeholder has requested guidance providing 
that steps of an intermediated exchange will not be recast under 
Federal income tax principles if (i) the intermediary acts on its own 
account in acquiring distributing corporation debt from third parties 
(that is, the intermediary becomes the owner of such debt for Federal 
income tax purposes and the acquisition is not funded or guaranteed by 
the distributing corporation), (ii) the intermediary assumes the risk 
that the distributing corporation may default on its debt while such 
debt is held by the intermediary, and (iii) the distributing 
corporation debt acquired by the intermediary was not issued with a 
purpose of avoiding the requirements or limitations of section 361.
    Another stakeholder has recommended that the Treasury Department 
and the IRS refrain from issuing substantive guidance given the fact-
intensive nature of determining whether an intermediated exchange 
should be recast. The stakeholder has recommended that the IRS continue 
to issue private letter rulings on a case-by-case basis to taxpayers 
that are able to establish an intermediary's status as a creditor 
acting for its own account by reference to the factors specified in a 
series of technical advice memoranda previously issued by the IRS. See 
T.A.M. 8815003 (Dec. 11, 1987); T.A.M. 8738003 (May 22, 1987); T.A.M. 
8735007 (May 18, 1987); T.A.M. 8735006 (May 18, 1987).
2. Direct Issuances
    Stakeholders have provided various recommendations to the Treasury 
Department and the IRS regarding the treatment of direct issuance 
transactions. Stakeholders uniformly have contended that the proposed 
regulations should recast or recharacterize a direct issuance 
transaction only if the transaction presents an abuse within the 
meaning of section 361(b)(3). In addition, stakeholders consistently 
have contended that the policy of section 361 confirms that direct 
issuance transactions satisfy the requirements for nonrecognition 
treatment under section 361. Although one stakeholder has acknowledged 
that, in some circumstances, the Treasury Department and the IRS may 
have a legitimate concern that a direct issuance transaction should be 
treated as a sale of controlled corporation stock to the intermediary, 
the stakeholder has noted that delineating the exact bounds of an 
abusive transaction as it relates to section 361(b)(3) and (c)(3) would 
be difficult. Accordingly, stakeholders generally have recommended that 
the Treasury Department and the IRS continue to address the section 361 
qualification of direct issuance transactions through the IRS's private 
letter ruling program rather than through Treasury regulations.
    Alternatively, stakeholders have recommended that the proposed 
regulations set forth specific safe harbors for direct issuance 
transactions that, after adequately taking into account commercial 
considerations (which one stakeholder has referred to as ``commercially 
grounded carveouts''), clearly would not present evidence of abuse. One 
stakeholder has recommended that a direct issuance transaction be 
respected as a borrowing if: (i) the newly issued debt qualifies as 
debt for Federal income tax purposes; (ii) the new debt issuance and 
the exchange agreement with the intermediary (regarding satisfaction of 
the newly issued debt with controlled corporation stock or securities) 
are pursuant to two legally separate agreements; (iii) the distributing 
corporation is not under economic compulsion to satisfy the newly 
issued debt with controlled corporation stock or securities at the time 
of issuance because the distributing corporation has sufficient other 
resources to repay the debt; (iv) the newly issued debt is satisfied 
with controlled corporation stock or securities having a fair market 
value equal to the principal amount and unpaid interest on the debt; 
and (v) the distributing corporation retains tax ownership of the 
controlled corporation stock or securities until the time of repayment.
    Another stakeholder has suggested additional factors to be 
considered, including (i) the number of days the newly issued debt is 
outstanding before the exchange of that debt for controlled corporation 
stock or securities, and (ii) whether the intermediary participating in 
the direct issuance transaction is a member of a syndicate of lenders 
that has historically provided debt financing to the distributing 
corporation. Additionally, a stakeholder has recommended (i) limiting 
permissible direct issuance transactions to situations in which the 
proceeds of the new debt are used to retire historical debt, and (ii) 
including a general anti-avoidance rule based on the distributing 
corporation's business purpose for entering into the direct issuance 
transaction.

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C. Proposed Regulations

1. Overview
    The Treasury Department and the IRS continue to be of the view 
that, under certain circumstances, intermediated exchanges and direct 
issuance transactions can be recast or otherwise recharacterized under 
Federal income tax principles. Certain stakeholders have described the 
aforementioned concerns of the Treasury Department and the IRS with 
respect to such transactions as new or as deriving primarily from 
direct issuance transactions or refinancing transactions.
    However, these concerns are neither new nor unique. As confirmed 
almost a century ago by the Supreme Court in Gregory v. Helvering, the 
application of substance over form and other general Federal income tax 
principles is inseparable from the application of the Code itself. See 
also Newman v. Comm'r, 894 F.2d 560, 562 (2d Cir. 1990) (emphasizing 
that, ``in reviewing a transaction for tax consequences, the substance 
of the agreement takes precedence over its form''). Accordingly, one 
objective of these proposed regulations is to clarify that general 
Federal income tax principles apply with regard to the application of 
section 361 just as such principles would apply with regard to the 
application of other Code provisions.
    With regard to the application of section 361 to intermediated 
exchanges, the Treasury Department and the IRS note that concerns 
regarding agency and substance over form date back decades to a series 
of technical advice memoranda that considered the application of a 
prior version of section 108 of the Code to conceptually similar 
intermediated exchanges of stock and securities. See T.A.M. 8815003 
(Dec. 11, 1987); T.A.M. 8738003 (May 22, 1987); T.A.M. 8735007 (May 18, 
1987); T.A.M. 8735006 (May 18, 1987). The so-called ``5/14 standard'' 
in corporate private letter rulings developed out of concerns similar 
to those discussed in those memoranda. (Under this standard, rulings 
generally would be issued by the IRS if: (i) the intermediary purchased 
distributing corporation debt; (ii) after at least five days, the 
intermediary and the distributing corporation entered into an agreement 
to exchange the purchased distributing corporation debt for section 361 
consideration; and (iii) the exchange occurred at least 14 days after 
the intermediary purchased the distributing corporation debt.)
    With regard to the application of section 361 to direct issuance 
transactions, the Treasury Department and the IRS have expressed 
similar concerns for more than a decade. In particular, the Treasury 
Department and the IRS ceased considering certain private letter ruling 
requests under section 361 in part due to this type of section 361 
monetization transaction. See section 5.01(10) of Rev. Proc. 2013-3, 
2013-1 I.R.B. 113. As explained by Treasury Department and IRS 
officials at that time, these transactions raised issues concerning the 
application of general principles of Federal income tax, including the 
substance-over-form doctrine. Stakeholders also raised similar issues 
at that time.
    In addition, certain stakeholders have mischaracterized the 
concerns of the Treasury Department and the IRS as focused principally 
on (i) whether the new debt should be respected as a debt instrument 
for Federal income tax purposes, or (ii) temporal proximity. With 
regard to the former point, certain stakeholders have provided feedback 
on Notice 2024-38 emphasizing debt-equity factors or have noted that, 
outside of Federal income tax (for example, under securities law), new 
debt issued by a distributing corporation in a direct issuance 
transaction would be treated as debt.
    However, as previously discussed in this part IV.C.1, the Treasury 
Department and the IRS are concerned with the application of the Code 
and Federal income tax principles--not commercial law or other non-
Federal income tax law--to intermediated exchanges and direct issuance 
transactions. In particular, as expressed in Notice 2024-38, the 
concern is not simply the status of the newly issued distributing 
corporation debt as debt for Federal income tax purposes, but also that 
the form of those debt-elimination transactions should be respected and 
not recharacterized under Federal income tax principles.
    With regard to the latter point, the Treasury Department and the 
IRS replaced the 5/14 standard for private letter rulings in Rev. Proc. 
2018-53 with a standard based on a facts-and-circumstances analysis. 
This change was made due to concerns that the 5/14 standard provided a 
temporal requirement that was indifferent to the particular facts and 
circumstances of the transaction, including the intermediary's 
relationship with the distributing corporation. As a consequence, the 
Treasury Department and the IRS observed that the 5/14 standard created 
confusion for taxpayers as to whether temporal proximity is the sole 
consideration with regard to the application of agency or substance-
over-form principles to intermediated exchanges and direct issuance 
transactions.
    The Treasury Department and the IRS also continue to be of the view 
that Rev. Rul. 2017-9 and other revenue rulings mentioned by 
stakeholders in their submitted feedback do not (and cannot) set forth 
broadly applicable principles that would dictate the positions set 
forth in these proposed regulations. One reason is that there are long-
established limitations on the precedential value of revenue rulings. 
Specifically, ``[r]evenue rulings published in the [Internal Revenue] 
Bulletin do not have the force and effect of Treasury Department 
regulations (including Treasury Decisions), but are published to 
provide precedents to be used in the disposition of other cases, and 
may be cited and relied upon for that purpose.'' Section 
601.601(d)(2)(v)(d) of the Statement of Procedural Rules (codifying 
section 7.01(4) of Rev. Proc. 89-14, 1989-8 I.R.B. 20). In addition, 
``[e]ach revenue ruling represents the conclusion of the Service as to 
the application of the law to the entire statement of facts involved,'' 
as opposed to an application outside of that entire statement of 
relevant facts. Section 601.601(d)(2)(v)(d) (codifying section 7.01(6) 
of Rev. Proc. 89-14). Based on these limitations, ``taxpayers, Service 
personnel, and others concerned are cautioned against reaching the same 
conclusion in other cases unless the facts and circumstances are 
substantially the same.'' Section 601.601(d)(2)(v)(e).
    Another reason is that, in almost all instances, the facts and 
circumstances set forth in the revenue rulings mentioned by 
stakeholders are not substantially the same as the transaction facts 
considered by the Treasury Department and the IRS in developing these 
proposed regulations. See Rev. Rul. 2017-9 (providing that ``[t]his 
revenue ruling provides guidance regarding the federal tax treatment of 
certain transactions referred to as `north-south' transactions,'' 
rather than intermediated exchanges or direct issuance transactions); 
Rev. Rul. 59-197, 1959-1 C.B. 77 (considering the potential effect of a 
``cash sale to the key employee'' of the distributing corporation on 
section 355 qualification, rather than an intermediated exchange or a 
direct issuance transaction). Accordingly, those revenue rulings 
address entirely different provisions of the Code. See Rev. Rul. 2017-9 
(addressing the application of, and qualification under, sections 301, 
351, 355, and 361(b)(1) and (2) (not section 361(b)(3) and (c)(3)); 
Rev. Rul. 59-197 (addressing the application of the device

[[Page 5244]]

and continuity of interest requirements under section 355, not section 
361(b)(3) and (c)(3)).
    However, the Treasury Department and the IRS are of the view that 
the facts and analysis set forth in Rev. Rul. 79-258 are relevant for 
purposes of developing proposed regulations under section 357(b). 
Accordingly, based on a de novo consideration of the analysis set forth 
in that revenue ruling, proposed Sec.  1.357-3(d)(4)(ii)(B) would 
incorporate that analysis into proposed rules regarding the assumption 
by a controlled corporation of distributing corporation debt issued in 
close proximity to a divisive reorganization. See the discussion in 
part VIII.C.3.b of this Explanation of Provisions. For the reasons 
discussed in this part IV.C.1, the Treasury Department and the IRS do 
not view it as appropriate for these proposed regulations to extend the 
analysis of Rev. Rul. 79-258 to proposed rules addressing the 
application of section 361.
2. General Approach of Proposed Regulations
    The Treasury Department and the IRS appreciate the feedback 
received from stakeholders on intermediated exchanges and direct 
issuance transactions. As emphasized in Notice 2024-38, and consistent 
with other aspects of these proposed regulations, the proposed rules 
addressing these topics are intended (i) to be consistent with all 
relevant provisions of the Code (that is, the compliance objective); 
(ii) to provide certainty to taxpayers and the IRS regarding the 
application of all relevant provisions of the Code to purported section 
355 transactions (that is, the increased certainty objective); and 
(iii) to be responsive to the manner in which section 355 transactions 
are engaged in by taxpayers and reflect current market practices and 
preferences (that is, the transaction facilitation objective), to the 
extent that doing so does not conflict with the compliance and 
increased certainty objectives.
    With regard to the increased certainty objective, the Treasury 
Department and the IRS have leveraged the expertise of IRS audit and 
examination personnel to develop proposed rules that, to the extent 
practicable, employ bright-line safe harbors, objectively verifiable 
conditions for qualification, and other similar architecture that can 
be readily reflected on Form 7216. These rules reflect the express 
delegation of authority to the Secretary to prevent avoidance of tax 
through abuse of section 361(b)(3) or (c)(3). The Treasury Department 
and the IRS have endeavored to balance this increased certainty 
objective with the transaction facilitation objective.
3. Specific Aspects of Proposed Regulations
a. General Requirements for Deemed Distribution Treatment
    Proposed Sec.  1.361-5 would implement section 361(b)(3) and (c)(3) 
by setting forth requirements that, if satisfied, would cause a 
transfer of section 361 consideration by the distributing corporation 
to its creditor to be treated as a distribution by the distributing 
corporation to its shareholders pursuant to the plan of reorganization. 
First, the creditor of the distributing corporation must be a 
qualifying creditor, as determined under proposed Sec.  1.361-5(b). 
Second, the distributing corporation debt that is satisfied with 
section 361 consideration must constitute eligible distributing 
corporation debt, as determined under proposed Sec.  1.361-5(c)(2). 
Third, the amount of distributing corporation debt that can be 
eliminated under the safe harbors of section 361(b)(3) and (c)(3) 
cannot exceed a maximum amount, as determined under proposed Sec.  
1.361-5(d). Lastly, the transfer by the distributing corporation of 
section 361 consideration in exchange for eligible distributing 
corporation debt must be carried out as part of a qualifying debt 
elimination transaction, as determined under proposed Sec.  1.361-5(e).
    Notwithstanding the satisfaction of the foregoing requirements, 
proposed Sec.  1.361-5(f)(1)(i) would provide that the amount of 
section 361 consideration treated as transferred by the distributing 
corporation to a creditor of the distributing corporation in a 
qualifying debt elimination transaction is reduced by the amount of 
distributing corporation debt that is transitorily eliminated. See the 
discussion in part VII.C of this Explanation of Provisions regarding 
transitorily eliminated distributing corporation debt.
b. Qualifying Creditors
    Proposed Sec.  1.361-5(b)(1) would require each creditor to which 
the distributing corporation transfers section 361 consideration in a 
divisive reorganization to be a creditor that holds eligible 
distributing corporation debt (as described in proposed Sec.  1.361-
5(c)). Additionally, proposed Sec.  1.361-5(b)(1) and (b)(2)(i) 
generally would prohibit the distributing corporation from satisfying 
eligible distributing corporation debt held by a person related (within 
the meaning of section 267(b) or section 707(b)(1)) (see proposed Sec.  
1.361-1(b)(47)) to the distributing corporation (distributing 
corporation related person), the controlled corporation (controlled 
corporation related person), or a related person with regard to a 
distributing corporation related person or a controlled corporation 
related person (collectively, non-qualifying creditors). Creditors that 
hold eligible distributing corporation debt, and that are not otherwise 
disqualified as non-qualifying creditors under proposed Sec.  1.361-
5(b)(2), are referred to as ``qualifying creditors.''
    Proposed Sec.  1.361-5(b)(2)(ii) would provide an exception to the 
general related-creditor prohibition in proposed Sec.  1.361-5(b)(2)(i) 
for a creditor that is a distributing corporation related person or a 
related person with regard to a distributing corporation related person 
if three requirements are satisfied. First, as part of the plan of 
reorganization, proposed Sec.  1.361-5(b)(2)(ii)(A) would provide that 
the section 361 consideration must be transferred to a creditor that is 
neither a distributing corporation related person nor a related person 
with regard to a distributing corporation related person (unrelated 
ultimate creditor). Specifically, if the section 361 consideration is 
money or other property, proposed Sec.  1.361-5(b)(2)(ii)(A)(1) would 
provide that it must be transferred to an unrelated ultimate creditor 
pursuant to the plan of reorganization no later than the end of the 12-
month period beginning on the date the distributing corporation 
receives the money or other property (as appropriate). If the section 
361 consideration is qualified property (as defined in proposed Sec.  
1.361-1(b)(43)), proposed Sec.  1.361-5(b)(2)(ii)(A)(2) would provide 
that it must be transferred to an unrelated ultimate creditor in an 
expeditious manner pursuant to the plan of reorganization under 
proposed Sec.  1.368-4(d)(3). Second, proposed Sec.  1.361-
5(b)(2)(ii)(B)(1) would provide a general provision that all debt for 
which section 361 consideration is exchanged must be in existence as of 
the earliest applicable date. Proposed Sec.  1.361-5(b)(2)(ii)(B)(2) 
would provide that distributing corporation debt held directly by a 
distributing corporation related person or a related person with regard 
to a distributing corporation related person must qualify as historical 
distributing corporation debt described in proposed Sec.  1.361-
5(c)(2)(i). Third, proposed Sec.  1.361-5(b)(2)(ii)(C) would provide 
that each transaction (including each intermediate and unrelated 
ultimate creditor transfer), creditor (including the unrelated ultimate

[[Page 5245]]

creditor), and debt satisfied with section 361 consideration must be 
identified and described in the plan of reorganization with regard to 
the divisive reorganization.
    For purposes of the requirements in proposed Sec.  1.361-
5(b)(2)(ii)(A), proposed Sec.  1.361-5(b)(2)(ii)(A)(3) would permit one 
or more intermediate transfers of section 361 consideration between or 
among distributing corporation related persons or related persons with 
regard to distributing corporation related persons to satisfy debts 
(including the initial distributing corporation debt) if those 
intermediate transfers culminate in a transfer of section 361 
consideration to an unrelated ultimate creditor. Under proposed Sec.  
1.361-5(b)(2)(iii), a person's status as a distributing corporation 
related person or a controlled related person, or as a related person 
with regard to any distributing corporation related person or as a 
related person with respect to any controlled corporation related 
person, would be determined at the time of that person's receipt of the 
section 361 consideration in exchange for the satisfaction and 
retirement of debt in a transfer or series of transfers described in 
proposed Sec.  1.361-5(b)(2)(ii)(A).
c. Eligible Distributing Corporation Debt
i. In General
    Proposed Sec.  1.361-5(c)(1) would provide that distributing 
corporation debt is not eligible to be satisfied with section 361 
consideration under proposed Sec.  1.361-5(a) unless that debt 
qualifies as eligible distributing corporation debt.
(a) Historical Distributing Corporation Debt
    In general, proposed Sec.  1.361-5(c)(2)(i) would provide that 
distributing corporation debt that qualifies as historical distributing 
corporation debt is eligible to be satisfied with section 361 
consideration. In general, distributing corporation debt qualifies as 
historical distributing corporation debt if that debt was incurred 
before the ``earliest applicable date,'' and that debt has an original 
term that ends after the date of the exchange described in Sec.  1.361-
2(a) or 1.361-3(a) and is identified in the plan of reorganization or 
original plan of reorganization (if amended). The ``earliest applicable 
date'' is defined in proposed Sec.  1.361-1(b)(27) as the earliest date 
of three specified events: (i) the date of the first public 
announcement (as defined in Sec.  1.355-7(h)(10)) of the divisive 
reorganization or a similar transaction; (ii) the date the distributing 
corporation entered into a written agreement to effectuate the divisive 
reorganization or a similar transaction; and (iii) the date the 
distributing corporation's board of directors approved the divisive 
reorganization or a similar transaction.
    However, the Treasury Department and the IRS are of the view that a 
debt refinancing exception would be appropriate to help achieve the 
transaction facilitation objective. Specifically, proposed Sec.  1.361-
5(c)(2)(ii) would provide that distributing corporation debt incurred 
by the distributing corporation after the earliest applicable date is 
treated as historical distributing corporation debt only if the 
following four requirements are met. First, proposed Sec.  1.361-
5(c)(2)(ii)(A) would provide that the distributing corporation debt 
must be (i) a refinancing of historical distributing corporation debt, 
or (ii) a refinancing of refinanced historical distributing corporation 
debt (that is, the debt must be traced directly through one or more 
refinancings to debt that qualifies as historical distributing 
corporation debt). Second, proposed Sec.  1.361-5(c)(2)(ii)(B) would 
provide that the refinanced historical distributing corporation debt 
must not have been incurred as part of a plan to incur debt in addition 
to historical distributing corporation debt determined under proposed 
Sec.  1.361-5(c)(2)(i) (or an amount of debt in addition to the amount 
of historical distributing corporation debt determined under paragraph 
(d) of that section, without regard to proposed Sec.  1.361-
5(d)(2)(iv)) in anticipation of the divisive reorganization (for 
example, the incurrence of the refinanced historical distributing 
corporation debt would have occurred without regard to the divisive 
reorganization). Third, proposed Sec.  1.361-5(c)(2)(ii)(C) would 
provide that the distributing corporation must engage in a qualifying 
debt elimination transaction solely under proposed Sec.  1.361-5(e)(3) 
or (4) to eliminate that refinanced historical distributing corporation 
debt. Fourth, proposed Sec.  1.361-5(c)(2)(ii)(D) would provide that 
the qualifying debt elimination transaction must be described and 
identified in the plan of reorganization or original plan of 
reorganization (if amended) for the divisive reorganization.
    Proposed Sec.  1.361-5(c)(2)(iii) would provide that a revolving 
credit agreement to which the distributing corporation is a debtor 
qualifies as historical distributing corporation debt only if the 
following requirements are met. First, the distributing corporation 
must have entered into the agreement before the earliest applicable 
date. Second, the agreement does not expire until after the date of the 
exchange described in proposed Sec.  1.361-2(a) or 1.361-3(a). Third, 
the agreement is identified in the plan of reorganization or original 
plan of reorganization (if amended). The Treasury Department and the 
IRS request comments regarding whether there are other arrangements 
similar to revolving credit agreements that, based on the same 
rationale employed by these proposed regulations, should be treated 
similarly.
(b) Qualifying Trade Payables
    Proposed Sec.  1.361-5(c)(2)(iv) would provide that qualifying 
trade payables are eligible to be satisfied with section 361 
consideration. For purposes of that qualification, the following 
requirements must be met. First, the trade payables must be described 
in a plan of reorganization or original plan of reorganization (if 
amended). Second, the trade payables must have been incurred in the 
ordinary course of business of the distributing corporation. Third, the 
satisfaction of such trade payables is necessary (A) to ensure the 
allocation to the controlled corporation of all liabilities properly 
associated with the business assets transferred to that corporation and 
(B) to result in the controlled corporation being allocated liabilities 
in an amount that properly relates to its business operations, the 
earnings of which will be used to properly satisfy those liabilities.
(c) Direct Issuance Debt
    These proposed regulations would also provide that direct issuance 
debt is eligible to be satisfied with section 361 consideration. 
Specifically, proposed Sec.  1.361-5(c)(2)(v) would provide that direct 
issuance debt incurred as part of a direct issuance transaction (as 
defined in proposed Sec.  1.361-1(b)(17)) satisfying the requirements 
of proposed Sec.  1.361-5(e)(4) is eligible to be satisfied with 
section 361 consideration. See the discussion in part IV.C.3.d.iv 
regarding qualifying direct issuance transactions.
ii. Amount of Distributing Corporation Debt Repaid
    Under proposed Sec.  1.361-5(d)(1), the maximum amount of 
distributing corporation debt that can be satisfied with section 361 
consideration under proposed Sec.  1.361-5(a) would equal the amount 
obtained by subtracting the aggregate amount of distributing 
corporation debt that the controlled corporation assumes (in accordance 
with proposed Sec. Sec.  1.357-2 through 1.357-4) pursuant to the plan 
of reorganization from the lesser of (i) the

[[Page 5246]]

aggregate amount of distributing corporation debt (as determined under 
proposed Sec.  1.361-5(c)(3)), and (ii) the aggregate amount of 
distributing corporation debt determined under the eight-quarterly-
average test set forth in proposed Sec.  1.361-5(d)(2). The Treasury 
Department and the IRS are of the view that incorporating the IRS's 
long-standing, quarterly average test for advance ruling purposes 
(which was expanded to an eight-quarterly-average test in Rev. Proc. 
2018-53 to provide a more accurate determination) into this computation 
would help achieve the increased certainty objective of these proposed 
regulations.
(a) Aggregate Amount of Distributing Corporation Debt
    Under proposed Sec.  1.361-5(c)(3)(ii), the aggregate amount of 
distributing corporation debt would include solely the amounts 
described in proposed Sec.  1.361-5(c)(3)(ii)(A) through (E), as 
applicable, taking into account any reduction required by proposed 
proposed Sec.  1.361-5(c)(3)(iii) (that is, offsetting debts). 
Specifically, proposed Sec.  1.361-5(c)(3)(ii)(A) would provide that 
the aggregate amount of historical distributing corporation debt would 
equal the aggregate remaining principal amount, as of the earliest 
applicable date, of all historical distributing corporation debt other 
than historical distributing corporation debt that is eliminated as 
part of a qualifying direct issuance transaction. With regard to 
refinanced distributing corporation debt, proposed Sec.  1.361-
5(c)(3)(ii)(B) would provide that, if the distributing corporation 
relies on the refinancing exception for historical distributing 
corporatrion debt under proposed Sec.  1.361-5(c)(2)(ii), then the 
amount of that debt distributing corporation debt would equal the 
lesser of (i

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