Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.
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.
Ager
Bryan J
BJ
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Bourque
Laura E
LE
Buchner
Kay M
KM
Woerpel
K A
KA
D000498:Allyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
D000498:Allyl Compounds; D012821:Silanes; D013440:Sulfides