Thermolysis and photolysis of N-benzoylhydrazone derivatives

Abstract

Two selected N-benzoylhydrazones were subjected to thermolysis by refluxing at 200 °C. Benzil, benzoic acid, biphenyl, benzanilide together with the corresponding ketones, nitriles, substituted methanes, and imines were isolated. Similar treatment of a third hydrazone at 250 °C afforded, in addition to the previous products, toluene, bibenzyl, stilbene, and 2-phenylindole. Photolysis of the same hydrazones in acetonitrile gave the previously reported products but in different ratios along with azine derivatives and substituted methanes. A free radical mechanism involving homolysis of the N-N and C-N bonds is suggested, substantiated by trapping of the phenyl radical with isoquinoline, to account for the formation of the identified products. © 2011 Springer-Verlag.