Add time:08/16/2019         Source:sciencedirect.com

Thermolysis of O-phenylcarbamoyl benzophenone oxime (I) leads to the formation of N2, NH3, CO2, benzene, biphenyl, aniline, azobenzene, benzonitrile, benzanilide, carbanilide, benzophenone, benzophenone-N-phenylimine and 2-phenylbenzoxazole. Analogous results are also obtained on thermolysis of O-phenylcarbamoyl acetophenone oxime (II) together with products characteristic of the methyl group, namely, acetophenone, 2-methylbenzoxazole and acetophenone-N-phenylimine. Also, thermolysis of O-phenylcarbamoyl benzoylphenyl ketoxime (III) under the same conditions gives mostly similar products as from the benzoyl free radicals, namely, benzaldehyde and benzil. On the other hand, ultraviolet irradiation of oximes I and II in 2-propanol give rise to products of primary molecular homolysis which are: CO2, benzonitrile, biphenyl, aniline, benzanilide (or acetanilide), carbanilide and benzophenone (or acetophenone)-N-phenylimine. Similarly, ultraviolet irradiation of ketoxime III in 2-propanol gives rise to primary fragmentation products similar to those above together with the corresponding products of benzoyl radicals. Repeating the thermolysis of I in the presence of isoquinoline as a radical scavenger, 1-phenylisoquinoline is formed together with the normal products of pyrolysis. On UV irradiation of I in 2-propanol solvent and in the presence of benzophenone as photosensitizer, 1-hydroxyfluorene is formed together with the normal products of photolysis. From the results of ketoximes I–III thermolysis or photolysis and products separated, we can conclude that the molecules undergo homolysis of NO,OCO or CON bonds providing the corresponding radical intermediates. The radicals react by hydrogen abstraction, dimerization, disproportionation, fragmentation, and/or cyclization. Under thermolysis conditions, the primary products can undergo secondary multistage rearrangements.

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