Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes

Laura E. Bourque, Pamela A. Haile, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

Original languageEnglish (US)
Pages (from-to)7180-7182
Number of pages3
JournalJournal of Organic Chemistry
Volume74
Issue number18
DOIs
StatePublished - Sep 18 2009

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Silanes
Ethers
Cyclopentanes
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes. / Bourque, Laura E.; Haile, Pamela A.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 74, No. 18, 18.09.2009, p. 7180-7182.

Research output: Contribution to journalArticle

Bourque, Laura E. ; Haile, Pamela A. ; Woerpel, Keith. / Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 18. pp. 7180-7182.
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