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

doi:10.1021/jo070634p

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

Chemistry

Research output: Contribution to journal › Article › peer-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 π_cc by hyperconjugation.

Original language	English (US)
Pages (from-to)	6595-6598
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	17
DOIs	https://doi.org/10.1021/jo070634p
State	Published - Aug 17 2007

ASJC Scopus subject areas

Organic Chemistry

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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.",

author = "Kim, {Angie I.} and Kimmel, {Kyle L.} and Antonio Romero and Smitrovich, {Jacqueline H.} and Woerpel, {K. A.}",

year = "2007",

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volume = "72",

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AU - Kim, Angie I.

AU - Kimmel, Kyle L.

AU - Romero, Antonio

AU - Smitrovich, Jacqueline H.

AU - Woerpel, K. A.

PY - 2007/8/17

Y1 - 2007/8/17

N2 - (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.

AB - (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.

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

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