Three-Electron S_N2 Reactions of Arylcyclopropane Cation Radicals. 2. Steric and Electronic Effects of Substitution

摘要

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.