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Thermal and Photofragmentation of N ‐Benzoylhydrazone Derivatives
Author(s) -
Gaber Abd ElAal M.,
Mohamed Shaaban K.
Publication year - 1998
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199800115
Subject(s) - chemistry , benzil , bibenzyl , homolysis , isoquinoline , hydrazone , azine , acetonitrile , medicinal chemistry , benzoic acid , thermal decomposition , photodissociation , photochemistry , organic chemistry , radical , catalysis
Two selected benzoylhydrazones I and II were subjected to thermolysis by reflux at 200 °C. Benzil, benzoic acid, biphenyl, benzanilide together with the corresponding ketones, nitriles and imines were isolated. Similar treatment of the third hydrazone III at 250 °C afforded, in addition to the previous products, bibenzyl, stilbene, and 2‐phenylindole. Photolysis of the same hydrazones I‐III 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 phenyl radical with isoquinoline, to account for the formation of the identified products.