Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Autor: Ager BJ; Department of Chemistry, University of California, Irvine, California 92697-2025, USA., Bourque LE, Buchner KM, Woerpel KA
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2010 Aug 20; Vol. 75 (16), pp. 5729-32.
DOI: 10.1021/jo1008228
Abstrakt: 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.
Databáze: MEDLINE