PHOTOCHEMISTRY OF UNSATURATED NITROGEN CONTAINING COMPOUNDS .2. MECHANISM OF BENZONITRILE AND BENZALDIMINE FORMATION DURING IRRADIATION OF BENZALAZINE

The photochemical reaction of benzalazine (1) to give benzonitrile and benzaldimine (2) was studied in the presence of various hydrogen donors in an effort to obtain information which would determine whether the mechanism for this photochemical transformation is inter- or intramolecular. These studies showed that with the addition of effective hydrogen donating agents such as benzhydrol and decyl mercaptan a definite decrease in product yield occurred; however, a limiting value in the decrease of this yield was reached beyond which further addition of trapping agents had no effect. These results are'interpreted as indicative of both intra- and intermolecular reaction being operative in the photochemical conversion of benzalazine (1) to benzonitrile and benzaldimine (2). Mechanisms for these two processes are presented and discussed. © 1969, American Chemical Society. All rights reserved.