[2—(Arylmethyl) phenyl] carbenes with Ar= phenyl (16), l-naphthyl (20), and 2—furyl (24) have been generated photolytically from appropriate diazo or tosylhydrazone precursors. Intramolecular addition to the arene prevailed in pentane solution, insertion into art/10 C—H bonds of the arene being a minor process. On direct photolysis in methanol, intermolecular 0— H insertion predominated over intramolecular addition to phenyl and l-naphthyl groups ( ...