Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes

Bryan J. Ager; Laura E. Bourque; Kay M. Buchner; K. A. Woerpel

doi:10.1021/jo1008228

Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes

Bryan J. Ager, Laura E. Bourque, Kay M. Buchner, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Silylene transfer to allylic sulfides results in a formal 1,2-sulfide migration. The rearrangement yields substituted silacyclobutanes, not the expected silacyclopropanes. The silacyclobutanes were elaborated by insertions of carbonyl compounds selectively into one carbon-silicon bond. A mechanism for the 1,2-sulfide migration is proposed involving an episulfonium ion intermediate.

Original language	English (US)
Pages (from-to)	5729-5732
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	16
DOIs	https://doi.org/10.1021/jo1008228
State	Published - Aug 20 2010

ASJC Scopus subject areas

Organic Chemistry

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title = "Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes",

abstract = "Silylene transfer to allylic sulfides results in a formal 1,2-sulfide migration. The rearrangement yields substituted silacyclobutanes, not the expected silacyclopropanes. The silacyclobutanes were elaborated by insertions of carbonyl compounds selectively into one carbon-silicon bond. A mechanism for the 1,2-sulfide migration is proposed involving an episulfonium ion intermediate.",

author = "Ager, {Bryan J.} and Bourque, {Laura E.} and Buchner, {Kay M.} and Woerpel, {K. A.}",

year = "2010",

month = aug,

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language = "English (US)",

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T1 - Silylene transfer to allylic sulfides

T2 - Formation of substituted silacyclobutanes

AU - Ager, Bryan J.

AU - Bourque, Laura E.

AU - Buchner, Kay M.

AU - Woerpel, K. A.

PY - 2010/8/20

Y1 - 2010/8/20

N2 - Silylene transfer to allylic sulfides results in a formal 1,2-sulfide migration. The rearrangement yields substituted silacyclobutanes, not the expected silacyclopropanes. The silacyclobutanes were elaborated by insertions of carbonyl compounds selectively into one carbon-silicon bond. A mechanism for the 1,2-sulfide migration is proposed involving an episulfonium ion intermediate.

AB - Silylene transfer to allylic sulfides results in a formal 1,2-sulfide migration. The rearrangement yields substituted silacyclobutanes, not the expected silacyclopropanes. The silacyclobutanes were elaborated by insertions of carbonyl compounds selectively into one carbon-silicon bond. A mechanism for the 1,2-sulfide migration is proposed involving an episulfonium ion intermediate.

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Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes

Abstract

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