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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.

SUBMITTER: Ager BJ

PROVIDER: S-EPMC4037888 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Ager Bryan J BJ Bourque Laura E LE Buchner Kay M KM Woerpel K A KA

The Journal of organic chemistry 20100801 16

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. ...[more]

PMID: 20704444

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