Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes

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

Research output: Contribution to journalArticlepeer-review


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 languageEnglish (US)
Pages (from-to)5729-5732
Number of pages4
JournalJournal of Organic Chemistry
Issue number16
StatePublished - Aug 20 2010

ASJC Scopus subject areas

  • Organic Chemistry


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