Reaction of Benzyl and Naphthylmethyl Esters with Arene Radical Anions

Article abstract of DOI:10.1021/jo00063a027

The reactions of four esters, naphth-1-ylmethyl acetate, naphth-1-ylmethyl benzoate, benzyl acetate, and benzyl benzoate, with the salts of radical anions of fluoranthene and biphenyl have been studied.When ester radical anion formation is energetically possible, CH2-O bond cleavage 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 side reactions.In most cases, these processes compete with the initial reduction and cleavage.