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.
Graphical abstract