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
- and -naphthols beside the previous products. Also heating of I under reflux boiling tetralin lead to
the formation of 1-hydroxytetralin, -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.