PHOTOCHEMICAL HYDROLYSIS OF N-SUBSTITUTED IMINS

The benzophenone-sensitized photolysis of benzaldehyde anil in anhydrous alcoholic solvents in an atmosphere of oxygen leads mainly to the formation of benzaldehyde and aniline. The incorporation of oxygen has been shown not to involve direct attack on the substrate but rather the formation of water and hydrogen peroxide. Each of these reagents can effect the photo-sensitized hydrolysis of the anil, but the contribution by water is minor compared to that by hydrogen peroxide. Other minor products formed in the reaction are 1,2,N,N′-tetraphenylethylenediamine and 2-phenylquinoline. Other imines are shown to undergo similar photochemical hydrolysis. © 1968.