The Journal of Organic Chemistry

Kinetics and regioselectivity of ring opening of substituted cyclopropylmethyl radicals

ALJ Beckwith, VW Bowry

Index: Beckwith, Athelstan L. J.; Bowry, Vincent W. Journal of Organic Chemistry, 1989 , vol. 54, # 11 p. 2681 - 2688

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Citation Number: 76

Abstract

Accurate analysis of the mixture of hydroxylamines 8 formed when suitable peroxides 4 undergo homolysis in the presence of the nitroxyl radical 1, 1, 3, 3-tetramethylisoindolin-2- yloxy (T) has afforded rate constants for ring opening of the cyclopropylmethyl radicals 2a, 2c, 2dc*, 2dtmw, and 2e and cyclization of the, but-3-enyl radicals la, IC, and Id. The presence of methyl substituents enhances the rates both of cyclization and of ring opening ...