Photolysis of Some N-Arylbenzamidoximes in Acetonitrile

The photolysis of five N-arylbenzamidoxime derivatives I-V in dry acetonitrile gives rise to anilides 8 and benzimidazoles 1 as the major products in addition to benzonitrile 4, arylamines 5, benzoic acid 6, and 2-phenyl benzoxazoles 7. In the presence of naphthalene, I gave α- and β-naphthols 2 and 3 beside the previous 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. This photodegradation process can be considered as an alternative method for the synthesis of anilide, benzimidazole and benzoxazole derivatives in addition to other organic compounds.