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. The photodegradation of some N‐arylbezamidoximes I‐V found to be an alternative pathway for the synthesis of some oragnic comounds namely anilides 8, benzimidazole 1 and benzoxazole 7 derivatives. The isolated products have been interpreted in the terms of free radical mechanism involving the homolysis of N‐O and/or C‐N bonds.