Three-Electron SN2 Reactions of Arylcyclopropane Cation Radicals. 2. Steric and Electronic Effects of Substitution1
Journal of the American Chemical Society1997Vol. 119(5), pp. 994–1004
Citations Over TimeTop 10% of 1997 papers
Abstract
The nucleophilic substitution reactions on substituted arylcyclopropane cation radicals were studied by a combination of methods including product studies, time-resolved laser flash photolysis, kinetic isotope effects, and quantum chemical calculations. The reactions were found to proceed stereospecifically with inversion of configuration, with high regioselectivity for nucleophilic attack at the more substituted carbon atom, and with very small steric effects. Electronic effects on the nucleophilic substitution regiochemistry and the rate constants were found to be substantial for substituents on the cyclopropane moiety and on the aryl ring.
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