Abstract
Thermolysis of N-phenylbenzamide oximes I, II and III (R = Cl, NO2 and OCH3) under nitrogen gives rise to benzimidazoles as the major products (45-52%), in addition to benzonitrile, arylamines, benzoic acid, phenols, benzanilides, 2-phenyl benzoxazoles and carbazoles. In the presence of naphthalene, I gave alpha- and beta-naphthols beside the previous products. Also heating of 1 under reflux boiling tetralin lead to the formation of 1-hydroxytetralin, alpha-tetralone and 1,1'-bitetralyl as the major products. The isolated products have been interpreted in the terms of a free radical mechanism involving the homolysis of N-O and/or C-N bonds. Crown Copyright (C) 2011 Published by Elsevier B.V. All rights reserved.