Bc. Shi et Rd. Guthrie, REACTION OF BENZYL AND NAPHTHYLMETHYL ESTERS WITH ARENE RADICAL-ANIONS, Journal of organic chemistry, 58(11), 1993, pp. 3067-3071
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.