Trapping and identification of the intermediate aryl radicals from the reaction of aroylarylhydrazines (arylarenecarbohydrazides) with sodium hydride

Abstract

Treatment of N-aryl-N′-aroylhydrazines (N-arylarenecarbohydrazides) with sodium hydride in the presence of oxygen afforded biphenyls and arylcarboxylic acids in good yields. E.s.r. trapping techniques have demonstrated conclusively the formation of phenyl and other radicals in high concentrations. The reaction is compared with the previously known simple oxidation of hydrazines.