Reaction of Phenylhydroxylamine with Bisulfite. A Possible Model for Amine-Mediated Carcinogenesis

Article abstract of DOI:10.1021/jo00149a012

Under anaerobic conditions, phenylhydroxylamine reacts with the model nucleophile (bi)sulfite to form aniline, o- and p-aminophenol, and o- and p-aminobenzenesulfonate.Evidence is presented suggesting that all products result from intermediates formed from nucleophilic attack of both bisulfite and sulfite on the arylhydroxylamine with subsequent covalent addition-elimination processes leading to products.Such a scheme offers a possible alternative pathway for describing the mechanism for carcinogenic arylation of nucleic acid residues by arylhydroxylamines not requiring the intermediacy of short-lived free radicals or nitrenium ions.