Mechanistic studies of the allylic rearrangements of α-silyloxy allylic silanes to silyloxy vinylic silanes

Angie I. Kim, Kyle L. Kimmel, Antonio Romero, Jacqueline H. Smitrovich, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Mechanistic evidence suggests that the Lewis acid-promoted allylic rearrangement of α-silyloxy allylic silanes proceeds along an ionic reaction pathway involving a contact ion pair. The driving force for this transformation is alleviation of steric congestion at the allylic position of the α-silyloxy allylic silane and stabilization of πcc by hyperconjugation.

Original languageEnglish (US)
Pages (from-to)6595-6598
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number17
DOIs
StatePublished - Aug 17 2007

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Silanes
Lewis Acids
Stabilization
Ions

ASJC Scopus subject areas

  • Organic Chemistry

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Mechanistic studies of the allylic rearrangements of α-silyloxy allylic silanes to silyloxy vinylic silanes. / Kim, Angie I.; Kimmel, Kyle L.; Romero, Antonio; Smitrovich, Jacqueline H.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 72, No. 17, 17.08.2007, p. 6595-6598.

Research output: Contribution to journalArticle

Kim, Angie I. ; Kimmel, Kyle L. ; Romero, Antonio ; Smitrovich, Jacqueline H. ; Woerpel, Keith. / Mechanistic studies of the allylic rearrangements of α-silyloxy allylic silanes to silyloxy vinylic silanes. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 17. pp. 6595-6598.
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