The thermal desulfination of allylic sulfonyl halides

Malcolm D. King, Rodney E. Sue, Rodney H. White, David J. Young

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Allylic sulfonyl halides can be generated by halogenolysis of the corresponding triorganotin sulfinates. Allylic sulfonyl bromides and iodides undergo a first order, thermal desulfination with allylic rearrangement to yield the corresponding allylic halides. The desulfination of a cyclic allylic sulfonyl bromide is stereospecific, proceeding with γ-syn bromine migration.

Original languageEnglish
Pages (from-to)4493-4496
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number25
DOIs
Publication statusPublished - 23 Jun 1997
Externally publishedYes

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Bromides
Hot Temperature
Bromine
Iodides

Cite this

King, Malcolm D. ; Sue, Rodney E. ; White, Rodney H. ; Young, David J. / The thermal desulfination of allylic sulfonyl halides. In: Tetrahedron Letters. 1997 ; Vol. 38, No. 25. pp. 4493-4496.
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The thermal desulfination of allylic sulfonyl halides. / King, Malcolm D.; Sue, Rodney E.; White, Rodney H.; Young, David J.

In: Tetrahedron Letters, Vol. 38, No. 25, 23.06.1997, p. 4493-4496.

Research output: Contribution to journalArticleResearchpeer-review

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AU - King, Malcolm D.

AU - Sue, Rodney E.

AU - White, Rodney H.

AU - Young, David J.

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AB - Allylic sulfonyl halides can be generated by halogenolysis of the corresponding triorganotin sulfinates. Allylic sulfonyl bromides and iodides undergo a first order, thermal desulfination with allylic rearrangement to yield the corresponding allylic halides. The desulfination of a cyclic allylic sulfonyl bromide is stereospecific, proceeding with γ-syn bromine migration.

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