Molecular Rearrangements. XXVIII. Thermolysis and Photolysis of Some Hydroxamic Acid Derivatives

Article abstract of DOI:10.1246/bcsj.61.2629

Thermolysis and photolysis of benzohydroxamic acid and some of its derivatives have been investigated.Thermolysis of benzohydroxamic acid (BHA) either by heating in air or in a sealed tube gives NH3, H2O, CO, benzil, aniline, o- and p-aminophenols, phenoxazine, benzanilide, and benzoic acid.Whereas, thermolysis of N-(benzyloxy)benzamide (BBA) affords toluene, benzaldehyde, bibenzyl, stilbene, phenanthrene, acridine, and o- and p-aminodiphenylmethane in addition to the previous products.Analogous products were also obtained on pyrolysis of phenylacetohydroxamic acid.Photolysis of BHA and BBA in acetonitrile gives similar results to those of pyrolysis.A free-radical mechanism involving homolysis at different sites was postulated to account for the formation of such products.