Nucleophilic character of bridgehead free radicals

Abstract Bridgehead free radicals have been produced in equimolecular mixtures of benzene and p -difluorobenzene by the thermal decomposition of the t-butylperoxyesters of 1-adamantyl, 1-bicyclo[2,2,2]octyl and 1-biciclo[2.2.1]heptyl carboxylic acids. The reactivity of p -difluorobenzene relative to benzene indicated that bridgehead radicals possess nucleophilic character.