CARACTERE POLAIRE DU RADICAL PHENYL-2 CYCLOPROPYLE: REGIOSELECTIVE DE LA REACTION SUR LA FONCTION PEROXYACIDE

Article abstract of DOI:10.1016/0040-4020(82)85154-5

A study of the reactivity of the 2-phenylcyclopropyl radicals obtained by thermal decomposition of 2-phenycyclopropane carboxylic peracids in benzene or cyclohexane solution is presented.It was found that these reactions led to the formation of phenylcyclopropane and its corresponding acid and not to the formation of 2-phenycyclopropanol.It appeared that the stereochemistry of the starting peracid did not influence the course of these reactions.These results led us to conclude that the 2-phenylcyclopropyl radical was very weakly nucleophilic towards the O-O peracid bond and that it reacted essentially by H-abstraction.Its low nucleophilicity which is similar to that of the phenyl radical but most likely lower than that of the bicyclo<2.2.1> 1-heptyl radical is probably due to its pyramidal structure.