PHOTOCHEMISTRY OF ORTHO-PHENOXYMETHYL-SUBSTITUTED ARYL AZIDES : A NOVEL NITRENE REARRANGEMENT EN ROUTE TO ISOLABLE IMINOQUINONE METHIDES?

The answer to the question in the title is: probably yes. A surprising reaction is observed upon photolysis of aryl azide 1 in the presence of diethylamine. The iminoquinone methide 2 is isolable and is probably formed by a shift of the phenoxy group to the nitrene center followed by nucleophilic attack of diethylamine and elimination of phenol.