Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a di-tert-butylsilylene source

Pamela A. Cleary, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) In examining the scope of the di-rert-butylsilylene transfer to gem-disubstituted alkenes to form silacyclopropanes, we discovered an unprecedented reaction of homoallylic ethers. When silylene transfer was performed at room temperature or above, two di-rert-butylsilylene units were incorporated into the molecule, and complete rearrangement of the carbon backbone occurred. This report describes the scope of this unique reaction as well as the mechanistic studies conducted that led to a proposed mechanism.

Original languageEnglish (US)
Pages (from-to)5531-5533
Number of pages3
JournalOrganic Letters
Volume7
Issue number24
DOIs
StatePublished - Nov 24 2005

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Gems
Silanes
Ethers
Alkenes
silanes
ethers
Carbon
Metals
Molecules
Temperature
metals
alkenes
carbon
room temperature
molecules
di-tert-butylsilylene

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a di-tert-butylsilylene source. / Cleary, Pamela A.; Woerpel, Keith.

In: Organic Letters, Vol. 7, No. 24, 24.11.2005, p. 5531-5533.

Research output: Contribution to journalArticle

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