REACTION OF BENZYL AND NAPHTHYLMETHYL ESTERS WITH ARENE RADICAL-ANIONS

The reactions of four esters, naphth-1-ylmethyl acetate, naphth-1-ylme thyl benzoate, benzyl acetate, and benzyl benzoate, with the salts of radical anions of fluoranthene and biphenyl have been studied. When es ter radical anion formation is energetically possible, CH2-O bond clea vage follows rapidly. The resultant ArCH2 radical is reduced under the reaction conditions. The ArCH2 anion thus produced can react with the ester both as a nucleophile and as a base to promote a variety of sid e reactions. In most cases, these processes compete with the initial r eduction and cleavage.