Journal of Organic Chemistry p. 57 - 60 (1983)
Update date:2022-07-31
Topics:
Sternson, L.A.
Dixit, A.S.
Becker, A.R.
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.
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Doi:10.1021/ja00269a017
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