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, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Mechanistic studies of the allylic rearrangements of α-silyloxy allylic silanes to silyloxy vinylic silanes'. Together they form a unique fingerprint.

Cite this