Kinetic Analysis of the Rearrangement of a Conformationally Constrained α-Cyclopropylbenzyl Radical

Hariharan Venkatesan; Marc M. Greenberg

doi:10.1021/jo00092a003

Kinetic Analysis of the Rearrangement of a Conformationally Constrained α-Cyclopropylbenzyl Radical

Research output: Contribution to journal › Article › peer-review

Abstract

Modulation of the cyclopropylmethyl (CPM)/homoallyl radical equilibrium by phenyl substitution at the radical center is exploited in determining the kinetic versus thermodynamic preference for bond scission in a bicyclic CPM radical. Exocyclic ring opening is determined to be 28.7 times faster than the respective endocyclic process. This method will be of general use for determining the regioselectivity of radical rearrangements.

Original language	English (US)
Pages (from-to)	3514-3517
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	59
Issue number	13
DOIs	https://doi.org/10.1021/jo00092a003
State	Published - Jul 1 1994
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00092a003

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title = "Kinetic Analysis of the Rearrangement of a Conformationally Constrained α-Cyclopropylbenzyl Radical",

abstract = "Modulation of the cyclopropylmethyl (CPM)/homoallyl radical equilibrium by phenyl substitution at the radical center is exploited in determining the kinetic versus thermodynamic preference for bond scission in a bicyclic CPM radical. Exocyclic ring opening is determined to be 28.7 times faster than the respective endocyclic process. This method will be of general use for determining the regioselectivity of radical rearrangements.",

author = "Hariharan Venkatesan and Greenberg, {Marc M.}",

year = "1994",

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N2 - Modulation of the cyclopropylmethyl (CPM)/homoallyl radical equilibrium by phenyl substitution at the radical center is exploited in determining the kinetic versus thermodynamic preference for bond scission in a bicyclic CPM radical. Exocyclic ring opening is determined to be 28.7 times faster than the respective endocyclic process. This method will be of general use for determining the regioselectivity of radical rearrangements.

AB - Modulation of the cyclopropylmethyl (CPM)/homoallyl radical equilibrium by phenyl substitution at the radical center is exploited in determining the kinetic versus thermodynamic preference for bond scission in a bicyclic CPM radical. Exocyclic ring opening is determined to be 28.7 times faster than the respective endocyclic process. This method will be of general use for determining the regioselectivity of radical rearrangements.

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Kinetic Analysis of the Rearrangement of a Conformationally Constrained α-Cyclopropylbenzyl Radical

Abstract

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