Silylene Transfer to Allylic Sulfides: Formation of Substituted Silacyclobutanes

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 f...

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Veröffentlicht in:Journal of organic chemistry 2010-08, Vol.75 (16), p.5729-5732
Hauptverfasser: Ager, Bryan J, Bourque, Laura E, Buchner, Kay M, Woerpel, K. A
Format: Artikel
Sprache:eng
Schlagworte:
Allyl Compounds - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Kinetics and mechanisms
Miscellaneous
Molecular Structure
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
Sulfides - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1008228