The reactions of superoxide ion with arylhydrazines

Abstract

Arylhydrazines react with potassium superoxide to give a variety of products, most of which are derived from interaction of aryl radicals with the solvent. Phenylhydrazine in toluene gives three isomeric methylbiphenyls, diphenylmethane and bibenzyl. In pyridine, the products identified were 2-, 3- and 4-phenylpyridine. A more complex range of products was obtained from substituted phenylhydrazines. Products are consistent with a process in which superoxide ion abstracts hydrogen atoms from the hydrazines giving radical intermediates, including aryl radicals, which react with the solvents.