The thermal desulfination of allylic sulfonyl halides

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

doi:10.1016/S0040-4039(97)00911-8

The thermal desulfination of allylic sulfonyl halides

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

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	4493-4496
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(97)00911-8
Publication status	Published - 23 Jun 1997
Externally published	Yes

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title = "The thermal desulfination of allylic sulfonyl halides",

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.",

author = "King, {Malcolm D.} and Sue, {Rodney E.} and White, {Rodney H.} and Young, {David J.}",

year = "1997",

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AU - King, Malcolm D.

AU - Sue, Rodney E.

AU - White, Rodney H.

AU - Young, David J.

PY - 1997/6/23

Y1 - 1997/6/23

N2 - 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.

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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U2 - 10.1016/S0040-4039(97)00911-8

DO - 10.1016/S0040-4039(97)00911-8

M3 - Article

AN - SCOPUS:0030900460

VL - 38

SP - 4493

EP - 4496

JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

SN - 0040-4039

IS - 25

ER -

The thermal desulfination of allylic sulfonyl halides

Abstract

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