REACTION OF BENZYL AND NAPHTHYLMETHYL ESTERS WITH ARENE RADICAL-ANIONS

Authors
Citation
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
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
11
Year of publication
1993
Pages
3067 - 3071
Database
ISI
SICI code
0022-3263(1993)58:11<3067:ROBANE>2.0.ZU;2-7
Abstract
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.