Subsection 55(3.1)

Paragraph 55(3.1)(a)

Administrative Policy

2023 Ruling 2022-0958241R3 - Public Spin-Off Butterfly

pre-butterfly transactions included DC acquiring shares under a plan of arrangement

CRA ruled on a butterfly spin-off by a listed Canadian corporation (DC) of its indirect interest in a foreign project to a “SpinCo” to be held by its shareholders, with most of the steps to occur pursuant to a plan of arrangement. The completed pre-butterfly transactions included DC acquiring all the shares of a Canadian corporation that were not already held by it pursuant to a plan of arrangement.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(3.02) public company spin-off with s. 51 reversal of new s. 86 common shares 948
Tax Topics - Income Tax Act - Section 86 - Subsection 86(1) new common shares created on s. 86 reorg then immediately converted under s. 51 back to old common shares 124
Tax Topics - Income Tax Act - Section 89 - Subsection 89(1) - Public Corporation - Paragraph (b) public spinco to elect effective before its shares were listed 84
Tax Topics - General Concepts - Fair Market Value - Shares FMV of listed shares based on their 5-day VWAP pre-spin-off or post spin-off 173

2017 Ruling 2016-0674681R3 - Sequential Split-Up Butterfly

sale of securities for cash proceeds that are reinvested, and tendering shares for shares of offeror

Preliminarily to a butterfly distribution that was favourably ruled upon, DC1 sold portfolio investment units for cash, and may reinvest the proceeds in marketable securities or other investments – transactions that are represented to be independent of the butterfly transactions. It will also tender a small percentage stake in a public company for shares of the offeror.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution sequential split-up butterfly with 1% tolerance, triggering of capital gains to generate CDA and RDTOH, and year end change to accommodate RDTOH division 747
Tax Topics - Income Tax Act - Section 129 - Subsection 129(1) capital gain deliberately triggered to generate CDA and RDTOH addition and year end change granted to isolate dividend refund 543
Tax Topics - Income Tax Act - Section 249.1 - Subsection 249.1(7) CRA accommodates year end change so that dividend refund of full RDTOH balance is generated in Year 1 210

2014 Ruling 2014-0528291R3 - Butterfly Reorganization

preliminary and subsequent transactions

DC was not controlled by either of its two shareholders (WCo and SCo). Prior to a butterfly transfer to Newco, formed by SCo, DC will proceed with a sale of assets for cash equal to their fair market value. Following the butterfly, Newco will amalgamate with ECO, which is partly owned by SCo.

2013 Ruling 2013-0491651R3 - Cross-Border Butterfly

preliminary LP acquisition, cross-border debt repayments and dividend: not part of series
Background

Foreign PubCo will spin-off Foreign SpinCo to its shareholders. Foreign SpinCo is a great-grandchild subsidiary held by it "through" ForCo 1 and ForCo 2.) DC (a wholly-owned subsidiary of ForCo 2 and thus a "sister" of Foreign SpinCo) will effect a split-up butterfly of the Canadian portion of the Spin-Off Business to TC, a direct newly-incorporated Newco subsidiary of ForCo2. Activities directly carried on in Canada by other subsidiaries of DC, namely, B Co (whose commons shares also were held by ForCo11, a subsidiary of Foreign PubCo), C Co, D Co (wholly-owned by C Co), and LP 1 and E Co, the GP of LP 1 (the "DC Retained Business") are to be retained by DC after the Spin-Out.

Preliminary transaction (before ruled-upon butterfly transactions)
  • LP 1 was acquired by DC at a time that "the directors of DC had no knowledge or expectation of the Proposed Transactions," with such acquisition being represented to be part of the series which includes 3.
  • ForCo 10 (described in redacted para. 61 and likely owned outside the DC group) repaid debt owing to B Co, B Co paid a dividend to DC and ForCo11,and DC paid a dividend to ForCo2 with such transactions being represented not have been effected before the proposed transactions were contemplated.

See detailed summary under s. 55(1) - distribution.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution cross-border b/f with 3-party exchange, cash-out of ineligible shareholders, proportionate allocation of foreign spinco debt, pension liability classification, prelim non-series dividend 1011
Tax Topics - Income Tax Act - Section 55 - Subsection 55(3.1) - Paragraph 55(3.1)(b) - Subparagraph 55(3.1)(b)(i) cross-border b/f with 3-party exchange, pro rata application of upper tier debt, cash-out of ineligible shareholders 501
Tax Topics - Income Tax Act - Section 86 - Subsection 86(1) exchange for substantively identical common shares 124

7 October 2011 Roundtable, 2011-0399401C6 - Butterfly, life insurance policies, grandfathering

a policy loan under a life insurance policy to reduce its CSV would trigger s. 55(3.1)(a)

Two siblings are the shareholders of two transferee corporations which are to receive two life insurance policies taken out by the distributing corporation on the life of each sibling to fund the redemption of the other's shares on the other's death, with the cash surrender value (CSV) of each policy being treated as a cash or near cash asset, but with the CSVs of the two policies differing. Could a proportional division of the distributing corporation's cash or near cash assets be accomplished by borrowing on a policy so that its net worth equaled that of the other? CRA responded:

In general ... a loan made by a corporation technically results in an acquisition of cash by the corporation. Thus, in the particular situation described above, the CRA may consider that the acquisition of cash by the distributing corporation as a result of the loan would come within paragraph 55(3.1)(a) and would have the effect of subjecting intercorporate dividends to the application of subsection 55(2).

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution CSV of life insurance policy was a cash asset - FMV excess could be an investment asset if no cash-out intention 212
Tax Topics - Income Tax Act - Section 55 - Subsection 55(4) s. 55(4) inapplicable if the principal reason for parent’s control of DC was parent's economic interests 178

2000 Ruling 1999-0010723 - sequential butterfly reorganizations

A reallocation of mortgage balances in respect of two of the properties to be transferred would result in an acquisition of property by the distributing corporation in contemplation of a distribution even though both properties were properties of the same type for purposes of the distribution.

Income Tax Technical News, No. 16, 18 December 1998

discussion whether Parthenon would indicate that a distributing corporation would not be considered to control its subsidiaries if ultimate control was elsewhere.

14 June 1996 CTF Roundtable Q. 18, 9620790 - PRE-BUTTERFLY TRANSACTIONS

"Where the butterfly is being carried out on a 'net equity' basis, the repayment of a debt (whether owing to a third party or a shareholder) could be viewed as resulting in property becoming property of the distributing corporation in contemplation of the distribution, thus contravening paragraph 55(3.1)(a), where the repayment of the debt changes the mix of property of the distributing corporation."

Income Tax Regulation News, Release No. 3, 30 January 1995 under "Butterfly Reorganizations"

Where in contemplation of a butterfly, a corporation transfers property to a partnership in consideration for a partnership interest, the acquisition of the partnership interest will come within the prohibition in s. 55(3.1)(a). Similarly, where in contemplation of a butterfly, a corporation acquires property from a partnership, the acquisition will come within the prohibition in s. 55(3.1)(a).

Articles

Marshall Haughey, "Spinoff Butterflies in Trouble?", Canadian Tax Focus, Volume 3, No. 4, November 2013, p. 3.

Exchange of shares to DC on permitted exchange (p. 3)

As a pre-distribution step in a typical spinoff butterfly, shareholders of the distributing corporation exchange their common shares in the distributing corporation for new common and preferred shares in the distributing corporation on a tax-deferred basis under subsection 51(1) or 86(1). Such an exchange is a "permitted exchange" under subsection 55(1), provided that it does not result in an acquisition of control of the distributing corporation. Thus, one presumes that the exchange is unobjectionable under the butterfly rules in section 55. However, the share exchange may technically infringe paragraph 55(3.1)(a). If that is the case, paragraph 55(3)(b) will not operate to prevent the application of subsection 55(2).

Application of s. 55(3.1)(a) to permitted exchange? (p. 3)

Paragraph 55(3.1)(a) will cause paragraph 55(3)(b) not to apply where, in contemplation of and before a distribution made in the course of the reorganization in which the dividend was received, property became property of the distributing corporation otherwise than as a result of certain enumerated exceptions, none of which appears to apply to a share exchange. Thus, whether paragraph 55(3.1)(a) will apply to the share exchange turns on whether the old shares become property of the distributing corporation.

Acquisition by DC on permitted exchange (p. 3)

[I]t appears that corporate law does not preclude the possibility of the old shares becoming property of the distributing corporation on the share exchange.

CRA position (p. 4)

Notwithstanding the analysis above, the CRA does not appear to consider a share exchange objectionable: it has issued favourable rulings in the past (9813073 (1998) and 9727303 (1998)) when a share exchange took place as a pre-distribution step in a spinoff butterfly. These rulings were given before the November 26, 2004 Department of Finance comfort letter was issued. That letter was the impetus for the exclusion of public corporations from the application of paragraph 55(3.1)(a).

Firoz Ahmed, "Subsection 55(3) Update", Canadian Current Tax, Vol. 15, No. 8, May 2005, p. 69:

Discussion of effect of contractual agreements on property-becoming-property test in s. 55(3.1)(a).

Vance Sider, "Section 55: Administrative Developments", 1995 Corporate Management Tax Conference Report, c. 8.

Paragraph 55(3.1)(b)

Administrative Policy

22 January 2016 External T.I. 2015-0617601E5 F - Pipeline followed by butterfly

where pipeline transaction followed by split-up butterfly, the opco also is a distributing corporation

CRA considered transactions in which, during the second year of conventional pipeline transactions, the Newco ("Corporation 2") was split between the estate beneficiaries under a butterfly reorg:

  • The shares of the opco (“Corporation 1”), whose ACB was stepped up on death, are sold by the estate to its newly-incorporated Corporation 2 for high-PUC prefs (rather than the more usual note);
  • after the wind-up of Corporation 2 into Corporation 1 a year later under s. 88(1), the shares (both common and pref) of Corporation 1 are distributed to the two beneficiaries;
  • two months later, there is a split-up butterfly of Corporation 2 between the two newcos (Corporations 3 and 4) of the two beneficiaries, so that Corporations 3 and 4 between them continue to carry on the business which previously was carried on by Corporations 1 and 2. In the meantime during the year following the winding up of Corporation 1, there is no bulk redemption (“rachat massif”) of the prefs of Corporation 2 or the successor prefs of Corporations 3 and 4.

After concluding that s. 84(2) likely would not apply, CRA turned to the butterfly rules, and stated (TaxInterpretations translation):

We could argue that all the transactions related to the implementation of the pipeline structure, the winding-up of Corporation 1 and the dividends resulting from the redemptions occurring as part of the butterfly transaction would be part of the same series of transactions. Included in the transactions, there would be two distributions (as defined in subsection 55(1))…: the first distribution on the winding-up of Corporation 1…and the second on the butterfly transaction itself.

For purposes of paragraph 55(3.1)(b), there would be two distributing corporations…for purposes of determining if the dividends received in the course of the transactions for dividing the business between Corporation 3 and Corporation 4 came within the paragraph 55(3)(b) exception.

…[T]he distribution consisting of the winding-up of Corporation 1 into Corporation 2 would not need to come within the exception provided by paragraph 55(3)(b) because by virtue of paragraph 88(1)(d.1), such distribution would not generate an intercorporate dividend which was subject to subsection 55(2). However, none of the events stipulated in paragraph 55(3.1)(b) could occur in the course of the series taking into account that Corporation 1 and Corporation 2 should be the distributing corporations for purposes of determining if dividends received in the course of the transactions for dividing the business between Corporation 3 and Corporation 4 would come within the paragraph 55(3)(b) exception.

Furthermore, in addition to establishing if paragraph 55(3)(b.1) applied taking into account two distributing corporations and two transferee corporations, it would be necessary to examine if paragraphs 55(3.1)(a) , (c) and (d) applied to the transactions in the series taking into account one distributing corporation, namely Corporation 2, and two transferee corporations.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 84 - Subsection 84(2) pipeline transaction can be coupled with a butterfly split-up 468

8 October 2010 Roundtable, 2010-0373211C6 F - Butterfly Transaction - Permitted Exchange

issuance of shares by TC after the DC distribution without AOC of TC does not engage s. 55(3.1)(b)

Where after a butterfly transaction, a family trust (whose beneficiaries are persons unrelated to the transferee corporation, the distributing corporation and their shareholders) acquires an interest in one of the transferee corporations by subscribing for shares of the capital stock of the latter for a nominal value, does this contravene s. 55(3.1)(b) given that an issuance of shares is not a disposition? CRA responded:

[T]he issuance of treasury shares from the transferee corporation to the family trust is not a transaction within subparagraph 55(3.1)(b)(i) because of the issuance by a corporation of a share of its capital stock not constituting a "disposition" of property for the purposes of the Act as provided for in paragraph (m) of the definition of "disposition" in subsection 248(1).

Furthermore, subparagraph 55(3.1)(b)(iii) would not apply because, in the particular situation, there is an acquisition of shares of the capital stock of a transferee corporation made after the distribution was completed; and not an acquisition of shares of the capital stock of the distributing corporation in contemplation of the distribution.

Finally … to the extent that the control of the transferee corporation was not acquired by the family trust, subparagraph 55(3.1)(b)(ii) would also not be applicable.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Permitted Exchange - Paragraph (b) issuance of shares by TC after the DC distribution not relevant to there being “permitted exchange” 214

Articles

Christian Desjardins, Nik Diksic, "Cross-Border Butterflies in the Context of Public Spin-Off Transactions", 2015 CTF Annual Conference paper

History of s. 55(3.1)(b) (pp. 29:3)

[The main purpose of the original version of subsection 55(3.1) was to prevent…using the butterfly exemption rules to indirectly gain a treay exemption for a gain on a share sale that would not otherwise qualify for treaty protection. ...

[T]he changes proposed by the 1994 federal budget and as described in the Department of Finance explanatory notes accompanying the November 1994 draft legislation ensured that all purchase butterfly transactions (domestic and cross-border) would be denied the protection of the paragraph 55(3)(b) exemption. The new provisions also introduced a 10 percent de minimis exception to allow for sales and purchases by shareholders with insignificant interests... .

Denial of s. 55(3)(a) exemption (pp. 29:5)

[The following list] illustrates the basic manner in which a Canadian butterfly transaction is integrated into a cross-border spin-off. ...:

1) Foreign Pubco establishes Canadian Newco (the TC).
2) Foreign Pubco transfers shares of its Canadian subsidiary (the DC) with a FMV equal to the net FMV of the spin business to the TC.
3) DC transfers the spin business to the TC on a tax-deferred basis under subsection 85(1).
4) The TC shares owned by the DC, and the DC shares owned by the TC are cross-redeemed in exchange for promissory notes of equal value.
5) The promissory notes are set-off against each other and cancelled.
6) Foreign Pubco transfers its foreign spin assets to Foreign Spinco.
7) Foreign Pubco transfers the TC (which owns the spin business) to Foreign Spinco
8) The remaining spinoff steps are completed, and Foreign Spinco is ultimately distributed to the Foreign Pubco shareholders.

In [the base case outlined above]..., Foreign Pubco's gain or loss from the disposition of the spinoff shares is not included in computing its taxable income earned in Canada. In addition, the ultimate spinoff transaction is typically designed to be a tax-free transaction to Foreign Pubco (no recognition of gain or loss). As a result, paragraph 55(3.01)(e) deems Foreign Pubco to have disposed of those shares for proceeds that are less than FMV, and therefore the exemption in paragraph 55(3)(a) does not apply.

Requirement for Canadian spin business to represent under 10% of Foreign Spinco (pp. 29:8)

[T]he Canadian spin business must be relatively insignificant in the context of the overall spin-off and...other spin assets need to be contributed to Foreign Spinco before the contribution (or butterfly) of the Canadian spin business assets to ensure that the Foreign Spinco shares never derive 10 percent or more of their FMV from the TC shares. [fn 20: [The] 10 percent threshold must be maintained throughout the series of transactions-- for example, by ensuring that there are sufficient other assets in Foreign Spinco when it incorporates the TC. ...]

If the shares of Foreign Spinco derive 10 percent or more of their FMV from the Canadian spin business (or the shares of TC), then the transfer of the Foreign Spinco shares is subject to subclause 55(3.1)(b)(i)(A)(II), and therefore the paragraph 55(3)(b) exemption is unavailable. ...

No transfer of TC to a person (Foreign Spinco) who will cease to be related to Foreign Pubco (p. 29:8-10)

Another essential consideration that the Canadian separation transaction must satisfy to qualify under paragraph 55(3)(b) is that any transfer of the DC shares by Foreign Pubco must be a "permitted exchange". ...

Subparagraph 55(3.1)(b)(i) does not permit a transfer of the shares of the TC by a specified shareholder of the TC (i.e., Foreign Pubco) to a person who will cease to be related to the transferor as part of the series….

A potential solution to this issue is to slightly reorder the steps outlined above by establishing the TC under Foreign Spinco at the outset so that no subsequent transfer of the TC shares is required. The DC shares can then be transferred in sequential permitted exchanges from Foreign Pubco to Foreign Spinco and then to the TC. ...

Three-party exchange to address deemed transferee rule (pp. 29:11)

Adjusting the steps as illustrated... raises the issue of the deemed transferee rule in paragraph 55(3.2)(h)….[which] provides that each corporation that is a shareholder (and specified shareholder) of a DC at any time during the course of a series of transactions or events that includes a distribution is deemed to be a TC in relation to the DC. In the modified steps noted in figure 4, Foreign Spinco is deemed a TC if, at any time in the series, it was a shareholder of the DC… .

The solution…is the so-called three-party share exchange….

[F]oreign Pubco, Foreign Spinco, and the TC enter into a three-party share exchange agreement as follows:

1) Foreign Pubco transfers the DC shares directly to TC as consideration for the shares of Foreign Spinco issued in step 3.
2) The TC issues common shares to Foreign Spinco as consideration for the DC shares.
3) As consideration for the TC shares, Foreign Spinco issues shares to Foreign Pubco.

3-party exchange as permitted exchange (pp. 29:14-16)

These steps ...avoid the transitory acquisition of the DC shares by Foreign Spinco, which would otherwise qualify Foreign Spinco as a TC under paragraph 55(3.2)(h). The question, therefore, is whether a transfer that bypasses Foreign Spinco in this manner can still qualify as a permitted exchange.

The first requirement in the definition of "permitted exchange" is that there be an exchange of the DC shares for shares "of another corporation", which for the purposes of the provision is defined as "the acquiror". There is, however, no requirement that the acquiror be the corporation that actually acquires the DC shares. Instead, the only requirement is that the transferor (Foreign Pubco) receive shares of the acquiror as consideration for the transfer of the DC shares. ...

The second requirement is that no share of the capital stock of the acquiror outstanding immediately after the exchange be owned at that time by any person or partnership other than a participant. The only participant in figure 5 is Foreign Pubco, and Foreign Pubco owns all of the shares of Foreign Spinco immediately after the exchange. ...

The final requirement is that subparagraph (b)(iii) of the definition of permitted exchange apply. ...

As in the above example, if Foreign Pubco is the only DC shareholder and the only participant to the exchange, variables B and C are the same, and the fraction equals 1. As a result, the requirement in paragraph (b)(iii) is met. [fn 28: [I] t is often preferable to consolidate the DC shareholdings in the group in a single shareholder/participant immediately before the three-party share exchange. ...[P]ursuant to paragraph 55(3.2)(c) a person who acquires a share of the DC in contemplation of the butterfly distribution is deemed, in respect of the acquisition, not to be related to the person from whom it acquired the share, unless it acquired all of the shares of the DC that were owned by the other person. ...]

Substituted property issue under s. 55(3.1)(b)(i)(C) on 3-party exchange (pp. 29:16-17)

Clause 55(3.1)(b)(i)(C) examines, inter alia, whether the property (or substituted property) is acquired by a person who is unrelated to the vendor, or who ceases to be related to the vendor as part of the series, unless the property is acquired on a permitted exchange. ...

[I]t is unclear whether the Foreign Spinco shares qualify as property substituted for the DC shares. ...

[I]n our view, a subsequent disposition of substituted property that is acquired on a relevant excluded transaction (a permitted exchange, permitted acquisition or permitted redemption) should not be tested under clause 55(3.1)(b)(i)(C). Rather, a subsequent disposition of the property should be retested, starting with clause 55(3.1)(b)(i)(A). In this case, the Foreign Spinco shares do not qualify as property under this clause because they do not derive 10 percent or more of their FMV from the DC or TC shares; therefore, any disposition of them shares should not violate subparagraph 55(3.1)(b)(i). ...

We understand that this general interpretation has been accepted by the CRA, after consultation with the Department of Finance… .

Narrow meaning of “reorganization” in context of ss. 55(3.1)(b) to (d) (p. 29:18)

[T]he CRA has given a relatively narrow meaning to the term ["reorganization"] in this context:

[T]he "reorganization" referred to in section 55 would normally include only transfers of property by the distributing corporation to its shareholders (or corporations related to its shareholders) and the cross-redemption of shares or winding up of the distributing corporation. [fn 32:… 1996 Corporate Management Tax Conference ... 24:17-18.]

The CRA adopted this interpretation in the first cross-border butterfly ruling in 2006... with a specific statement in the comments section….

In the context of a cross-border butterfly, therefore, it is necessary to ensure only that the series of transactions or events does not include prohibited transactions or events described in 55(3.1)(a) or (b), and the continuity-of-interests rules in paragraphs 55(3.1)(c) and (d) should be largely irrelevant.

Reverse foreign spin-offs problematic (pp. 29:20-21)

Consider a reverse foreign spinoff, in which the keep assets are butterflied to the TC as part of the three-party share exchange, and the Foreign Spinco that is distributed to the Foreign Pubco shareholders is the existing shareholder of the DC.

In figure 6, Foreign Spinco (the existing shareholder of the DC) is a deemed TC under paragraph 55(3.2)(h), and therefore the transfer of its shares is problematic, regardless of whether the DC shares represent far less than 10 percent of the FMV of Foreign Spinco. Unlike the more typical transaction outlined above, here the new Foreign Keepco, rather than the existing Foreign Spinco, is a party to the three-party share exchange and therefore the shares of Foreign Spinco remain tainted and cannot be distributed outside the group without violating paragraph 55(3.1)(b). Furthermore, because Foreign Spinco is a deemed transferee corporation at the beginning of the series of transactions that includes the butterfly, it cannot easily (or perhaps ever) be cleansed of its TC status as part of the series. This … may not have arisen if, for example, Foreign Spinco held the DC shares through a single purpose foreign holding company. In this case, deemed TC status would extend only to that foreign holding company, and not to Foreign Spinco. Rather, Foreign Spinco would be tested only under the 10 percent de minimis rule… .

No rollover in 3-party exchange (p. 29:27)

If the transferred DC shares in a cross-border butterfly transaction are taxable Canadian property, any gain realized by the non-resident transferor is taxable under the Act (subject to possible application of a treaty exemption), unless the transfer is completed on a rollover basis under subsection 85(1). ...

Because the three-party share exchange is structured to ensure that the transferor (Foreign Pubco) does not receive the share consideration directly from TC, it may be difficult to take a seemingly opposite position in the context of subsection 85(1).

Non-application of s. 212.1 on 3-party exchange (p. 29:29)

Paragraph 212.1(1)(b) also provides that in computing the PUC of any shares issued by the purchaser corporation, the PUC may be reduced when any increase in the PUC in respect of the shares of purchaser corporation exists "by virtue of the disposition" of the subject shares. ... In the context of the three-party share exchange, the increase in the PUC in respect of the shares of TC issued to Foreign Spinco is clearly related to the disposition of the preferred shares of the DC. In other words, the increase exists "by virtue of the disposition" of the preferred shares of DC by Foreign Pubco to the TC. Consequently, the PUC of the newly issued shares of the TC will be limited to the PUC of the DC preferred shares pursuant to paragraph 212.1(1)(b).

Words and Phrases
reorganization

Subparagraph 55(3.1)(b)(i)

Administrative Policy

2014 Ruling 2014-0530961R3 - Cross-Border Butterfly

pro rata allocation of Foreign Spinco debt

In connection with a spin-off by a U.S. public company (Foreign PubCo) of a U.S. subsidiary (Foreign Spinco) to which one of its businesses was transferred, there was a butterfly split-up of an indirect Canadian subsidiary (DC) directly and indirectly holding Canadian portions of the two businesses in question, so that the Canadian transferee corporation (TCo) of DC was a subsidiary of Foreign Spinco. Following the Canadian butterfly transactions and before the spin-off by Foreign Pubco of Foreign Spinco, Foreign Spinco borrowed the "External Debt" from third party lenders (which did not relate to any particular assets of Foreign Spinco) and "distributed" the applicable portion thereof to Foreign Pubco so as to qualify as a tax-free distribution under Code s. 361(b). In connection with the s. 55(3.1)(b)(i)(A)(II) rule, CRA indicated that indebtedness of Foreign SpinCo will be considered to reduce the FMV of each property of Foreign SpinCo pro rata in proportion to the relative FMV of all property of Foreign SpinCo. See summary under s. 55(1) – distribution.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution U.S./Cda b/f including conversion of Foreign Spinco and TC from fiscally disregarded to regarded for Code purposes/2-stage transfer to TC of cash assets/post-b/f dividend by DC/s. 86.1 treatment/proportionate allocation of Foreign Spinco debt 1479
Tax Topics - Income Tax Act - Section 86.1 - Subsection 86.1(2) spin-off by U.S. pubco of U.S. spinco after Canadian butterfly 115

2013 Ruling 2013-0491651R3 - Cross-Border Butterfly

cross-border b/f with 3-party exchange, pro rata application of upper tier debt, cash-out of ineligible shareholders

Background

Foreign PubCo will spin-off Foreign SpinCo to its shareholders. Foreign SpinCo is a great-grandchild subsidiary held by it "through" ForCo 1 and ForCo 2). DC (a wholly-owned subsidiary of ForCo 2 and thus a "sister" of Foreign SpinCo) will effect a split-up butterfly of the Canadian portion of the Spin-Off Business to TC, a direct newly-incorporated Newco subsidiary of ForCo2. Activities directly carried on in Canada by other subsidiaries of DC, namely, B Co (whose commons shares also were held by ForCo11, a subsidiary of Foreign PubCo), C Co, D Co (wholly-owned by C Co), and LP 1 and E Co, the GP of LP 1 (the "DC Retained Business") are to be retained by DC after the Spin-Out.

Three-Party Exchange

Immediately prior to the distribution by DC and following a share capital reorganization of DC in which old common shares of DC will be exchanged for "DC New Common Shares" and "DC Special Shares", a three-party transfer agreement will be concluded between Forco 2, Foreign SpinCo and TC (a newly-incorporated Canadian subsidiary of Foreign SpinCo) in which: ( a) TC will agree to pay the purchase price for DC Special Shares transferred to it by ForCo 2 as described in para. (b) below by issuing TC Common Shares to Foreign SpinCo; (b) ForCo 2 will agree to pay the purchase price for the common shares issued to it by Foreign SpinCo as described in para. (c) below by transferring all of the DC Special Shares to TC; and (c) Foreign SpinCo will agree to pay the purchase price for the TC Common Shares issued to it by TC as described in para. (a) above by issuing common shares to ForCo 2.

Spin-Off

Following completion of the butterfly, Foreign PubCo will not distribute shares of Foreign SpinCo to shareholders who are domiciled in countries where Foreign SpinCo shares cannot be offered through the proposed Spin-Out, and to shareholders who hold a small number of Foreign SpinCo shares. Instead, it will issue the affected Foreign SpinCo share to an independent trustee who will sell them in the open market and distribute the net cash proceeds to such ineligible shareholders. Subject to the foregoing, Foreign PubCo will distribute the remaining outstanding shares in Foreign SpinCo pro rata to its shareholders under a scheme of arrangement on a proportionate basis.

Ruling

S. 55(3)(b) ruling is premised on 10% or more of the FMV of the Foreign SpinCo shares not, at any time, during the course the series being derived from the DC Special Shares or TC Common Shares. For these purposes, any indebtedness of Foreign SpinCo will be considered to reduce the FMV of each property of Foreign SpinCo pro rata in proportion to the relative FMV of all property of Foreign SpinCo.

See detailed summary under s. 55(1) - distribution.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution cross-border b/f with 3-party exchange, cash-out of ineligible shareholders, proportionate allocation of foreign spinco debt, pension liability classification, prelim non-series dividend 1011
Tax Topics - Income Tax Act - Section 55 - Subsection 55(3.1) - Paragraph 55(3.1)(a) preliminary LP acquisition, cross-border debt repayments and dividend: not part of series 230
Tax Topics - Income Tax Act - Section 86 - Subsection 86(1) exchange for substantively identical common shares 124

2012 Ruling 2011-0425441R3 - Cross Border Butterfly

upper tier debt applied pro rata re 10% limitation

Overview

A non-resident public company (Foreign Pubco) will be spinning off Business A to its shareholders, to be accomplished by a dividend-in-kind of its shares of Foreign Spinco (also non-resident) to its shareholders. Business B will be retained. Preliminarily to this spin-off, an indirect Canadian subsidiary of Foreign Pubco (Canco – which is the distributing corporation) will transfer the Canadian business relating to Business B as well as related foreign subsidiaries held directly (Forsub) or through a partnership (Forlp) and a partner thereof (Canco Sub 4) to the transferee corporation (TCo – a ULC). This will be facilitated through a direct transfer of the Newco holding company for such assets (Newsub) to TSub (a subsidiary of TCo), with TSub then being wound up into TCo. TCo (which will be directly held by Newco 3 and through transactions which are heavily redacted – see perhaps para. 122) will be indirectly transferred to Foreign Pubco, whereas Canco will become an indirect subsidiary of Foreign Spinco.

External borrowing

After the butterfly reorganization and before the spin-off of Foreign Spinco, Foreign Spinco will borrow money (the "External Debt") from arm's length lenders and use the proceeds to make a distribution to Foreign Pubco.

Application of 10% test

The butterfly ruling is given provided inter alia that xxx% or more of the fair market value "of the common shares of Foreign Spinco that Foreign Pubco owns was not, at any time during the course of any series of transactions or events…derived from the shares of Canco, TCo, Newco 3, Forco [or companies to which Newco 3 is transferred, namely, Newco 4 and New Holdco]."

The letter then states:

For the purposes of subclause 55(3.1)(b)(i)(A)(II), in determining whether XXX% or more of the FMV of the common shares of Foreign Spinco that Foreign Pubco owns was derived from the shares of Canco, TCo, Newco 3, Forco, Foreign Pubco, Newco 4 and New Holdco as described [above], the External Debt of Foreign Spinco…will be considered to reduce the FMV of each property of Foreign Spinco pro rata in proportion to the relative FMV of all property of Foreign Spinco.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution cross-border b/f with 3-party exchange to address s. 55(3.2)(h)/indemnity neutralizes liability assumption/Newco 3 is implicit DC 367

2012 Ruling 2012-0439381R3 - Cross-border spin-off butterfly

underline;">: Background. After preliminary transactions, DC becomes owned by Foreign Pubco. In order to accomplish a butterfly spin-off of the spin-off business of CD to a newly-incorporated subsidiary (TC) of a non-resident subsidiary of Foreign Pubco (Foreign Spinco Parent), various transactions occur including those set-out below.

DC and s. 86 reorganization

Each common share of DC will be changed into one redeemable retractable non-voting DC preferred shares (a DC New Preferred Share1) and one DC New Common Share.

Three-Party Share Exchange

In the context of a three-party transfer agreement (the "Three-Party Share Exchange") between Foreign Pubco, Foreign Spinco Parent and TC (a newly-incorporated Canadian subsidiary of Foreign Spinco Parent):

a) TC will agree to pay the purchase price for DC New Preferred Shares1 transferred to it by Foreign Pubco as described in para. (b) below by issuing TC Common Shares to Foreign Spinco Parent;

b) Foreign Pubco will agree to pay the purchase price for the common shares issued to it by Foreign Spinco Parent as described in para. (c) below by transferring all of the DC New Preferred Shares1 to TC; and

c) Foreign Spinco Parent will agree to pay the purchase price for the TC Common Shares issued to it by TC as described in para. (a) above by issuing common shares to Foreign Pubco (para. 66).

Permitted exchange

Immediately before the transfer of Newco common shares by DC to TC described below, the common shares of Foreign Spinco Parent (viewed as the "acquiror") owned by Foreign Pubco (viewed as the "participant") will have a fair market value that accords with the formula in (b)(iii) of the "permitted exchange" definition (para. 71).

Drop-down of Canadian Spin-off Business to Newco

DC will transfer its assets of the Spin-off Business to a newly-incorporated subsidiary (Newo) in consideration for assumption of liabilities and the issuance of common shares (para 74-75).

Butterfly distribution

. DC transfers its common shares of Newco to TC in consideration for TC preferred shares (para. 80).

Cross-redemption

TC will redeem its preferred shares, and DC will redeem the DC Preferred Shares1, in each case for a demand promissory note. Immediately thereafter, the principal amounts owing thereunder will be set-off against each other.

Spin-off by Foreign Pubco

Foreign Pubco will distribute all its shares of Foreign Spinco Parent to its shareholders as a dividend-in-kind.

Rulings

S. 55(2) will not apply to the deemed dividends arising on the cross-redemptions (referred to in Ruling D) provided that:

10% or more of the FMV of the Foreign Spinco Parent common shares that Foreign Pubco owns was not, at any time during the course of any series of transactions or events that includes the dividends described in Ruling D (a) and (b), derived from the DC New Preferred Shares1 or the TC Common Shares. (Ruling F)

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution cross-border b/f as part of foreign spin-off including (U.K.?) demergers 822

2012 Ruling 2011-0431101R3 - Cross-border spin-off butterfly

As preliminary transactions to a butterfly distribution by DC, which is owned by a non-resident subsidiary (Foreign Sub 1) of a non-resident publicly-traded corporation (Foreign Pubco), each common share of DC will be changed into one redeemable retractable non-voting DC special share and one DC New Common Share.

Permitted exchanges/Three-Party Share Exchange

Foreign Sub 1 will concurrently make the following transfers of its shares of DC:

(i) transfer all the DC Special Shares to TC, a newly-incorporated private corporation subsidiary of Foreign Sub 1 (para. 126(a)) in consideration for the issue of common shares of TC; and

(ii) transfer all the DC New Common Shares to Foreign Sub 15, a newly-incorporated LLC subsidiary of Foreign Spinco 1 which, in turn will be a non-Canadian subsidiary of Foreign Sub 1 (para. 126(b)).

In connection with the transfer in (ii) above, Foreign Sub 1, Foreign Sub 15, and Foreign SpinCo 1 will enter into a three-party agreement (the "Three-Party Share Exchange"), whereby:

(a) Foreign Sub 15 will agree to pay the purchase price for the DC Common Shares transferred to it by Foreign Sub 1 by issuing membership interests in the capital of Foreign Sub 15 to Foreign SpinCo 1 having an aggregate FMV at that time equal to the aggregate FMV of the DC Common Shares so transferred to it by Foreign Sub 1 as described in [para. (b) below]...;

(b) Foreign Sub 1 will pay the purchase price for the Foreign SpinCo 1 Common Shares issued to it by Foreign SpinCo 1 as described in [para. (c) below], by transferring all of the DC Common Shares to Foreign Sub 15; and

(c) Foreign SpinCo 1 will agree to pay the purchase price for the membership interests in Foreign Sub 15 by issuing common shares to Foreign Sub 1 having an aggregate FMV at that time equal to the aggregate FMV of the membership interests in Foreign Sub 15 so issued by Foreign Sub 15 to Foreign SpinCo 1 described in para. (a) above.

Following a butterfly distribution by DC to TC, Foreign Sub 1 will then distribute all its shares of Foreign Spinco 1 to Foreign Pubco. Foreign Pubco will distribute all its shares of Foreign Spinco 1 to its shareholders as a dividend-in-kind. Accordingly, the shares of Foreign Spinco 1 will be disposed of by a specified shareholder of DC (Foreign Sub 1) to persons who are not related to Foreign Sub 1.

CRA's butterfly ruling indicates that s. 55(2) will not apply to the deemed dividends arising on the cross-redemptions (referred to in Ruling D) occurring on the butterfly reorganization provided that:

10% or more of the FMV of the Foreign SpinCo 1 Common Shares was not, at any time, during the course of the series of transactions or events that includes the dividends described in Ruling D, derived from the DC New Common Shares or derived from the membership interest in Foreign Sub 15....For the purposes of subclause 55(3.1)(b)(i)(A)(II), in determining whether 10% or more of the FMV of the common shares of Foreign SpinCo 1 was derived from the DC New Common Shares that Foreign Sub 15 owns or derived from the membership interest in Foreign Sub 15 that Foreign SpinCo 1 owns, as described in Ruling F(I) above, any indebtedness of Foreign SpinCo 1, that is not a secured debt and that is not a debt related to a particular property, will be considered to reduce the FMV of each property of Foreign SpinCo 1 (or indirectly the FMV derived from DC Common Shares owned by Foreign Sub 15) pro rata in proportion to the relative FMV of all property of Foreign SpinCo 1. (Ruling F)

Articles

David Carolin, Manu Kakkar, Paola D’Agostino, "To Redeem or Not To Redeem a Specified Shareholder: That Is the 55(3)(b) Question", Tax for the Owner-Manager, Vol. 23, No. 4, October 2023, p. 6

S. 55(3.1)(b)(i)(C) concern if the preferred shares of a related individual (Dad) are redeemed at the commencement of a butterfly (pp. 6-7)

  • The distributing company (“DC”) has three shareholders: Dad owning frozen preferred shares; and his two sons, each owning 50% of the common shares. Dad’s shares are redeemed and the sons then butterfly the DC assets to their respective transferee companies (“TCs”).
  • The three conditions in ss. 55(3.1)(b)(i)(A), (B), and (C) may be met, so that s. 55(3.1)(b)(i) applies to deny butterfly treatment:
  • S. 55(3.1)(b)(i)(A)(I) applies because the vendor (Dad) is disposing of shares of DC.
  • S. 55(3.1)(b)(i)(B) applies because the vendor is a specified shareholder of DC, i.e., Dad owns all the DC preferred shares.
  • S. 55(3.1)(b)(i)(C) may apply on the basis that the redemption of Dad’s preferred shares constitutes an acquisition of property by a person (DC) who ceased to be related to the vendor (Dad) as part of the series (DC will be wound-up as part of the series and, therefore, will cease to be related to Dad): it might be considered that this redemption entailed the acquisition of property by DC.

Potentially more robust result if Dad exchanges his prefs for voting prefs of TCs before he is redeemed (pp. 7-8)

  • There is greater certainty if Dad instead transfers his DC preferred shares to each of the TCs in consideration for voting shares of the TCs, with the TCs then redeeming those shares.
  • Since Dad will be related to the TCs both before and after the butterfly, the transfer by him of his DC preferred shares to the TCs will satisfy the test in s. 55(3.1)(b)(i)(C) that property not be acquired by a person (other than the vendor) who is not related to the vendor or ceased to be related as part of the series.
  • Regarding the acquisition by Dad of the TC shares, this benefits from the exclusion under s. 55(3.1)(b)(i)(C) for an acquisition of property by the vendor.
  • S. 55(3.1)(b)(iii)(A), which denies butterfly treatment where a TC, in contemplation of a butterfly, acquired shares of the DC from a person to whom the acquiror was not related, would be satisfied since Dad would be related to each TC.
  • S. 55(3.2)(c), which modifies s. 55(3.1)(b) by deeming any particular person who acquired a share of DC in contemplation of a distribution not to be related, for the purposes of that acquisition, to the person from whom it acquired the share, would be cured by s. 55(3.2)(c)(ii), which allows a carve-out where the particular person was related to the DC immediately after the butterfly, i.e., Dad would still control both TCs as well as the DC immediately after the butterfly through his voting shares of each TC.

Clause 55(3.1)(b)(i)(A)

Subclause 55(3.1)(b)(i)(A)(II)

Administrative Policy

2023 Ruling 2022-0943871R3 - Cross-border spin-off butterfly

s. 55(3.1)(b)(i)(A)(II) tested at Foreign Spinco level by applying its debt, that does not relate to specific assets, on a pro rata basis

Background

Foreign Pubco, the non-resident and publicly traded parent of the group, held DC (a taxable Canadian corporation, or “TCC”) through four stacked non-resident corporations (Forco 4, holding Forco 3, holding Forco 2, holding Forco 1). However, Foreign Services (a non-resident subsidiary held by Foreign Pubco through a wholly-owned subsidiary, namely, Foreign Holdco), held a percentage of the shares of Forco 3 and of Forco 4. Foreign Services held Foreign XX which, in turn, jointly owned Sub 1 with DC (as common shareholders).

Completed transactions

Foreign Services incorporated Foreign Spinco and Foreign Spinco incorporated TC (a TCC).

Proposed transactions
  1. After preliminary transactions to create and eliminate debt between Foreign XX and Foreign Services, Foreign Services will contribute the stock of Foreign XX and other assets to Foreign Spinco for common shares.
  2. Sub 1 will make a PUC distribution of (in the case of Foreign XX) cash and (in the case of DC) a note owing to it by DC and cash, so that the DC Note will be extinguished.
  3. Pursuant to a s. 86 reorganization of its capital, Forco 1 will exchange each of its DC common shares for one DC new common share and one DC preferred share, with the stated capital of the “old” common shares apportioned between the DC new common and preferred shares in proportion to their relative aggregate FMV.
  4. The DC new common and preferred shares of Forco 1 will be distributed up the chain to Forco 2, then Forco 3.
  5. Forco 3 will distribute those shares to Forco 4 and Foreign Services in proportion to their respective ownership interests.
  6. Forco 4 will distribute the shares so received by it to Foreign Services.
  7. Pursuant to a three-party transfer agreement between Foreign Services, TC and Foreign Spinco (is expressed to occur as a “permitted exchange” in accordance with the formula in (b)(iii) of the s. 55(1) definition), Foreign Services will transfer its DC preferred shares to TC for a purchase price equal to their FMV as follows:
    (a) TC will agree to pay the purchase price for the DC preferred shares transferred to it by Foreign Services by issuing TC common shares to Foreign Spinco, having an FMV equal to that of the DC preferred shares so transferred to it by Foreign Services;
    (b) Foreign Services will agree to pay the purchase price for the Foreign Spinco common shares issued to it in (c) below by transferring all of the DC preferred shares to TC; and
    (c) Foreign Spinco will agree to pay the purchase price for the TC common shares issued to it by issuing common shares to Foreign Services having an FMV equal to that of the TC common shares issued to it.
  8. DC will transfer all its assets relating to Spin Business (being the shares of Sub 1) to TC in consideration for the assumption of certain liabilities of DC and the issuance of TC preferred shares. Quite detailed guidance is provided on the types-of-property analysis, but it is noted that it is anticipated that DC will have only business property.
  9. DC and TC will redeem the preferred shares held by each in the other for notes, and the notes will be set off.
  10. After loan advance and repayment transactions, Foreign Services will distribute all of its common shares of Foreign Spinco to Foreign Holdco, which will distribute them to Foreign Pubco, which will distribute them to its shareholders.
Additional information

At no time, during the course of the series of transactions that includes the ruled-upon dividends, will 10% or more of the FMV of the shares of Foreign XXXXXXXXXX or of Foreign Spinco be derived from any of the shares of DC or TC.

The shares of DC will not be taxable Canadian property.

Rulings

Including that

  • On the three-party share exchange, s. 212.1(1.1)(a) will not apply to deem a dividend to be paid by TC, or to be received by Foreign Services and s. 212.1(1.1)(b) will apply such that the amount added to the PUC of the TC common shares on such exchange will not exceed the PUC, immediately before the exchange, of the DC preferred shares transferred to TC;
  • The s. 55(3)(b) exception will apply (premised inter alia on satisfaction of the 10% test referred to above).
  • For the purposes of s. 55(3.1)(b)(i)(A)(II), in determining whether 10% or more of the FMV of the Foreign Spinco common shares is derived from shares of TC or DC “any indebtedness of Foreign Spinco that is not a secured debt and that is not a debt related to a particular property will be considered to reduce the FMV of each property of Foreign Spinco pro rata in proportion to the relative FMV of all property of Foreign Spinco.”
Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 55 - Subsection 55(1) - Distribution cross-border butterfly with 3-corner agreement 360

Clause 55(3.1)(b)(i)(C)

Articles

David Carolin, Manu Kakkar, "Freezes and Butterflies: Who Said Freezes are Easy?", Tax for the Owner-Manager,” Vol. 25, No. 2, April 2025, p. 9

Inapplicability of s. 55(3.1)(b)(i) exception if post-butterfly freeze by TC entails only a subscription by trust for common shares (pp. 10-11)

  • Brother and Sister, who are 50-50 shareholders of DC, and who, by virtue of s. 55(5)(e)(i), are deemed to be unrelated, effect a split-up butterfly in favour of their respective TCs. In this context, s. 55(3.1)(b)(i) relevantly provides that, except in specific carve-out situations, any person who disposes of property within the butterfly series must be related to the acquirer of the property.
  • Furthermore, s. 55(3.1)(b)(i)(C) establishes a continuity rule requiring that where property is disposed of within the butterfly series in succession (i.e., where there is a disposition of property, substituted property, or of any further substituted property in a continuous sequence), the final acquirer in that chain must be related to the original vendor at the start of the succession.
  • If the TC of Brother effects an estate freeze in favour of a trust, it would appear that s. 55(3.1)(b) would not apply because the trust would subscribe for shares rather than receiving them in substitution for other shares - and that this could be the case even if some of the beneficiaries of the trust were not related persons.

Need for workaround if butterfly was preceded by distribution of DC out of trust (p. 11)

  • Suppose that before the butterfly, all the shares of DC were owned by Dad Trust, and that the shares of DC were rolled out to the two beneficiaries, being Brother and Sister, as the first step in the butterfly split-up between their TCs.
  • If Brother TC then acquires the common shares of Brother as part of a freeze transaction, such exchange would be part of a succession, so that the s. 55(3.1)(b)(i)(C) continuity rule would apply, and the acquisition by Brother TC would violate the s. 55(3.1)(b) rule since such acquiror (Brother TC) would not be related (pursuant to s. 55(5)(e)(iii)) to the vendor (Dad Trust) at the beginning of the succession.
  • A workaround would involve Brother freezing directly as part of the butterfly, so that Brother would transfer his common shares of DC to Brother TC in exchange for frozen preferred shares of Brother TC, with new shareholders then subscribing for common shares of Brother TC, but not so as to acquire control of Brother TC (which would violate s. 55(3.1)(b)(ii).)

Paragraph 55(3.1)(c)

Administrative Policy

2023 Ruling 2022-0958601R3 - Post Butterfly Transactions

post-butterfly sales of distributed shares by TC (or redemption in hands of DC of retained shares) were independent of the butterfly and did not engage s. 55(3.1)(c) (or (d))
Background

Xco is a corporation holding cash and shares of Yco. (Yco's other shareholders are management employees and their holding company. ) The shareholders of Xco are:

  • Aco Amalco, Dco Amalco and Eco Amalco. Which are owned respectively by three unrelated individuals (A, D and E) or their respective family or spouse’s trust;
  • A Son Company, which is owned by A’s son (“A Son) and trusts for his spouse or family; and
  • AA Co, which is an unrelated third party.

The Xco shares now held by Dco Amalco and Eco Amalco were, prior to the successive butterfly transactions described in 2020-0848061R3 (the “Sequential Butterflies”), held by a single corporation (KL Amalco which, in turn, was a successor by amalgamation to “Kco”), whose shareholders were Dco and Eco (essentially with the same ownership as that of Dco Amalco and Eco Amalco). However, in the third butterfly described in 2020-0848061R3, a pro rata portion of the assets of KL Amalco were spun-off to a transferee corporation (TC5) formed by Eco, and Eco and TC5 then amalgamated to form Eco Amalco, and Dco Amalco was formed by the amalgamation of Dco and a successor or by amalgamation of KL Amalco.

Aco Amalco was the successor by amalgamation to an historical owner of Xco shares (Aco).

Proposed transactions
  1. Dco Amalco will acquire Xco shares of Eco Amalco for two promissory notes.
  2. Yco will pay cash dividends to its shareholders.
  3. Xco will repurchase shares of Dco Amalco for cash, a promissory note and preferred shares of Xco.
  4. Xco will use share subscription proceeds received from A Son Company to repay the promissory notes in 1.
  5. Dco Amalco will repay the promissory note in 3.
  6. Xco will redeem the preferred shares issued by it in 3.
Representation

The Proposed Transactions will not be completed in contemplation of, or as part of the series of transactions or events that includes, the Sequential Butterflies. Each of the Proposed Transactions would have occurred regardless of whether the Sequential Butterflies were completed, with modifications required, and the Sequential Butterflies would have occurred regardless of whether the Proposed Transactions were subsequently implemented. The Proposed Transactions do not benefit from the Sequential Butterflies and the Sequential Butterflies will not be impacted in any manner whatsoever by the Proposed Transactions.

Purpose

At the time of the Sequential Butterflies, Xco was a stable self-sustaining investment for Dco Amalco and Eco Amalco and there was no intent to significantly change the nature of its activities or to make significant capital investments. Xco has seen growth in its business, permitting it to start considering making significant new investments in business opportunities. Dco Amalco and Eco Amalco are not interested in pursuing these significant new investment opportunities and the purpose of the proposed transactions is to enable Dco Amalco and Eco Amalco to exit their investment in Xco.

Ruling

Re the proposed transactions not causing s. 55(3.1) to apply to deny the s. 55(3)(b) exception to the relevant dividends arising on the Sequential Butterflies.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) post-butterfly sales and redemptions of shares received on the butterfly were not part of the same series 444

29 November 2016 CTF Roundtable Q. 2, 2016-0669651C6 - Computation of safe income

moratorium on providing interpretations on safe income allocation to discretionary dividend shares

CRA characterized hypothetical transactions involving the use of discretionary dividend shares as entailing a transfer of value from two related corporations to two unrelated persons, and noted that they thus departed from normal business standards and were not explicable without more facts.

Rather than commenting on the contrived presented facts, CRA commented more generally on discretionary shares, and indicated that it will no longer be commenting on safe income allocation questions until it has studied the area further, whose potential for value shifting and valuation difficulties it finds troubling. This moratorium respecting interpretive issues relating to the use of discretionary dividend shares does not detract from the Rulings Directorate being “open for business” with respect to other s. 55 issues relating to 55.

CRA was not receptive to a suggestion that safe income computations could be skipped in the simple case of a holdco/opco structure and no or limited differences in accounting versus taxable income, stating that it is the duty of taxpayers and their representatives to be careful making claims that a dividend is not subject to the application of s. 55(2).

2010 Ruling 2010-0357061R3 - Split-up butterfly

After describing the distribution of property by the distributing corporation (DC) to three transferee corporations (TC1, TC2 and TC3) under a reorganization that is ruled to qualify as a butterfly reorganization and which is later represented not to include an acquisition described in s. 55(3.1)(c) "which is not described herein," the ruling describes a co-ownership agreement that is entered into by TC1, TC2 and TC3:

The co-ownership agreement will indicate that: (i) the co-owners do not intend to create a partnership; (ii) no co-owners can act on behalf of another co-owner without obtaining prior consent from that co-owner; (iii) each co-owner has a well-defined separation of interests in and ownership of the properties subject to eh co-ownership agreement; (iv) a co-owner cannot charge and/or grant security over the co-owned properties as a whole (i.e. the other co-owner's interest) as each co-owner only has the right to deal with its own interest in the co-owned properties; (v) profit and loss is calculated by each co-owner individually and there is no mechanism in the agreement that deals with the allocation of profit or loss; and (vi) the liability of the co-owners is limited to their own expenses.

The ruling letter summary states that provided the representation that there is no partnership is accurate, the entering into of this co-ownership agreement will not taint the butterfly.

Locations of other summaries Wordcount
Tax Topics - Income Tax Act - Section 96 co-ownership not a partnership 233

3 October 2011 External T.I. 2011-0421341E5 - Paragraphs 55(3.1)(c) or (d)

before a distribution made in the course of a butterfly reorganization, Opco sells real estate used in operating its business (and representing more than 10% of the value of the business) to a non-related person for fair market value consideration consisting solely of cash. S. 55(3.1)(c) would not apply because the real property would not be described in s. 55(3.1)(c)(ii); and similarly s. 55(3.1)(d) would not apply. S. 55(3.1)(a) would not apply because of the exception in s. 55(3.1)(a)(iv)(C). 8 June 2005 Comfort Letter distinguished.

x1995 Tax Executives Institute Round Table, Q. 2, File No. 951074

S.55(3.1)(c) would apply to deny the protection of the butterfly exemption in a situation where a corporate 30% shareholder of the distributing corporation transfers the property received by it to a partnership between itself and its wholly-owned subsidiary, where the other shareholders of the distributing corporation were unrelated corporations.

31 July 1995 External T.I. 9518445 - 50731

Example of a problem arising because s. 55(3.1)(c)(ii)(B) is not modified by the parenthetical expression "(other than money and indebtedness that is not convertible into other property)".

Articles

David Carolin, Manu Kakkar, "Problematic Post-Butterfly Transferee Corporation Dispositions Involving Paragraph 55(3.1)(c): Part I", Tax for the Owner-Manager, Vol. 22, No. 2, April 2022, p. 3

Purpose of s. 55(3.1)(c) continuity-of-interest rule (p.3)

The underlying purpose of paragraph 55(3.1)(c) is to prevent a butterfly whereby a group of companies engages in a premeditated series of transactions that transfers assets from the distributing company (DC) to the transferee company (TC), with the intention, from the outset, of having the TC immediately sell those assets to an unrelated third party within the same series so that the shareholder can “cash out” or otherwise gain some type of tax benefit.

Technical issues (pp. 4-5)

Technical issues include:

  • Regarding the connecting factor in s. 55(3.1)(c)(i) that (to disqualify the butterfly) requires that the property be acquired from TC by a non-related person in the same series of transactions or events as the butterfly, s. 248(10) “is broad enough to catch any transactions that have some connection, however remote, with the butterfly” so “that a very conservative interpretation could preclude the TC from ever disposing of property received in the butterfly to a non-related person because the series seemingly continues in perpetuity.”
  • The carve-out from the above rule for dispositions of property to unrelated persons in the ordinary course of business creates difficulties of interpretation, for example, where “the taxpayer’s ‘ordinary business’ involves transactions that are large and relatively few in number.”
  • Respecting the accessing of a further carve-out (which applies inter alia where the property that is disposed of to unrelated persons as part of the series constitutes less than 10% of the FMV of all of the butterflied property -- ignoring for these purposes, money and indebtedness), the property so disposed of cannot exceed 10% of the total value of the butterflied property at any time after the butterfly and prior to the end of the series – so that even if the FMV of certain property constituted, for example, 7% of the total FMV on the disposition date, it might exceed 10% of the total FMV at some point between the butterfly date and the disposition date, so as to put the butterfly offside.

Subparagraph 55(3.1)(c)(ii)

Clause 55(3.1)(c)(ii)(B)

Administrative Policy

28 February 2002 External T.I. 2002-0120315 F - Butterfly Transactions

application of s. 55(3.1)(c)(ii)(B) to post-butterfly issuance to unrelated persons of shares by the distributed corporation/ tainting effect on one TC of post-butterfly sale by the other TC
1st situation (post-butterfly share issuance by distributed corporation)

In the first situation, Holdco made pursuant to a butterfly reorganization a pro rata distribution of its sole asset, i.e., shares of Pubco to arm’s length transferee corporations (TCs) which had been its shareholders, following which Pubco proceeded with a public issuance of shares to persons who were not related the TCs.

CCRA indicated that the newly issued Pubco shares would be property described in s. 55(3.1)(c)(ii)(B) because more than 10% of their FMV was attributable, after the distribution and before the end of the series, to property held by Pubco (i.e., property described in s. 55(3.1)(c)(ii)(C)) – and concluded if the share issuance did not satisfy the “de minimis rule” by their FMV exceeding 10% of the FMV of the Pubco shares received by any TC when distributed, then s. 55(3.1)(c) would apply to exclude access to the butterfly exception.

CCRA rejected a submission that in order for a property to be described in s. 55(3.1)(c)(ii)(B), more than 10% of its FMV must be attributable, after the distribution and before the end of the series, to a single property described in s. 55(3. 1(c)(ii)(A) (i.e., a property received by the TC on the distribution) or to a single property described in s. 55(3.1)(c)(ii)(C) (i.e., a property to which the FMV of a property received by the TC on the distribution is attributable in whole or in part during the series). Having regard to the English version and under a purposive interpretation, “property” in s. 55(3.1)(c)(ii)(B) was used in its collective sense.

CCRA also indicated that, under the de minimis rule:

[T]he determination of the FMV of property in the phrase "fair market value of property ... received by the transferee corporation on the distribution" provided for in or under paragraph 55(3.1)(c) must be made on the basis of the net FMV of the property (i.e., taking into account the liabilities of a distributing corporation assumed by a transferee corporation in the course of a distribution), where a distribution has been made using the net FMV method … .

2nd situation (post-butterfly sale by a TC)

The TCs receiving a butterfly distribution of the Pubco shares of Holdco are Aco and Bco receiving 20% (or $20,000 in FMV) and 80% (or $$80,000 in FMV), respectively of the Pubco shares, in proportion to their Pubco shareholdings. Immediately thereafter, Bco disposes of $8,000 of its Puco shares to a person unrelated to Aco.

Regarding the application of s. 55(3.1)(c)(ii)(A) to Aco, it would not apply because Aco retained all its Pubco shares. Since it was Pubco shares that were acquired by the persons unrelated to Aco and not property held by Pubco, s. 55(3.1)(c)(ii)(C) would not apply to that acquisition. However, s. 55(3.1)(c) nonetheless would apply on the basis of s. 55(3.1)(c)(ii)(C) since the Pubco shares acquired by the persons not related to Aco would be described in s. 55(3.1)(c)(ii)(B), i.e., more than 10% of their FMV would be attributable, after the distribution and before the end of the series, to property held by Pubco described in s. 55(3.1)(c)(ii)(C)). The de minimis rule would not apply since the FMV of the Pubco shares acquired by the unrelated persons would represent more than 10% of the FMV of the Pubco shares received by Aco ($20,000 x 10% = $2,000).

Regarding Bco, the acquisition of the Pubco shares by the unrelated persons would come within the de minimis rule, as the FMV of such shares ($8,000) did not represent more than 10% of the FMV of the Pubco shares received by Bco on the distribution ($80,000 x 10% = $8,000).

Modified 2nd situation 2nd situation (post-butterfly sale by a TC plus a small sale by the 2nd TC)

In addition to the transactions above, there also was a disposition by Aco, immediately after the butterfly reorganization, of a portion of its Pubco shares to an unrelated person for proceeds of $2,000.

Regarding Aco, CCRA indicated that since the Pubco shares acquired from Bco by persons unrelated to Aco would be described in s. 55(3.1)(c)(ii)(C), the 55(3.1)(c)(ii)(B) test would be satisfied so that the dividend received by Aco would not be excluded from the application of s. 55(2). The de minimis rule would not apply.

S. 55(3.1)(c)(ii)(B) and (C) would similarly apply Bco respecting the Pubco shares acquired from Aco by the unrelated persons.