Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes

J Org Chem. 2010 Aug 20;75(16):5729-32. doi: 10.1021/jo1008228.


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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Allyl Compounds / chemistry*
  • Molecular Structure
  • Silanes / chemical synthesis*
  • Silanes / chemistry*
  • Stereoisomerism
  • Sulfides / chemistry*


  • Allyl Compounds
  • Silanes
  • Sulfides