Silylene oxonium ylides: di-tert-butylsilylene insertion into C-O bonds

Laura E. Bourque, Pamela A. Haile, J. M N Loy, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Allylic ethers undergo insertions of silylenes into C-O bonds to form allylic silanes. Silylene insertion into C-O acetal bonds was also observed. Formation of silylene ylide intermediates led to [1,2]-Stevens rearrangement products as well as [2,3]-sigmatropic products depending upon the steric environment of the starting allylic ether.

Original languageEnglish (US)
Pages (from-to)5608-5613
Number of pages6
JournalTetrahedron
Volume65
Issue number28
DOIs
StatePublished - Jul 11 2009

Fingerprint

Silanes
Acetals
Ethers
Ether
hydronium ion
di-tert-butylsilylene

Keywords

  • Allylic silanes
  • Oxonium ylide
  • Silylene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Silylene oxonium ylides : di-tert-butylsilylene insertion into C-O bonds. / Bourque, Laura E.; Haile, Pamela A.; Loy, J. M N; Woerpel, Keith.

In: Tetrahedron, Vol. 65, No. 28, 11.07.2009, p. 5608-5613.

Research output: Contribution to journalArticle

Bourque, Laura E. ; Haile, Pamela A. ; Loy, J. M N ; Woerpel, Keith. / Silylene oxonium ylides : di-tert-butylsilylene insertion into C-O bonds. In: Tetrahedron. 2009 ; Vol. 65, No. 28. pp. 5608-5613.
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