The Journal of Organic Chemistry

Hydrolysis and iron (2+)-induced reduction of N-aryl-O-pivaloylhydroxylamines: aqueous solution chemistry of model carcinogens

M Novak, RK Lagerman

Index: Novak, Michael; Lagerman, Robert K. Journal of Organic Chemistry, 1988 , vol. 53, # 20 p. 4762 - 4769

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Citation Number: 32

Abstract

The N-aryl-0-pivaloylhydroxylamines, la-d, which serve as models for the carcinogenic metabolites of aromatic amines, decompose in aqueous media by heterolysis of the N-0 bond. Substituent effects on rates of reaction and products of the decomposition of la-c are entirely consistent with the intermediacy of a singlet nitrenium ion. The least reactive compound in the series N-(4-nitrophenyl)-O-pivaloylhydroxylamine(la) yields 4- ...