Reactivity and selectivity of nitrenium ions derived from ester derivatives of carcinogenic N-(4-biphenylyl) hydroxylamine and the corresponding hydroxamic acid

M Novak, MJ Kahley, E Eiger, JS Helmick…

Index: Novak, Michael; Kahley, Mary Jo; Eiger, Emily; Helmick, John S.; Peters, Hope E. Journal of the American Chemical Society, 1993 , vol. 115, # 21 p. 9453 - 9460

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Citation Number: 97

Abstract

Abstract: N-Acetyl-N-(sulfonatooxy)-4-aminobiphenyl (la) and N-(4-biphenylyl)-O- pivaloylhydroxylamine (IC) decompose in 5% CH3CN/H20, p= 0.5 M, at 20" C via rate- limiting N-0 bond heterolysis to generate the nitrenium ion intermediates 2a and 2b, respectively. Addition of C1-(10.5 M) or N3-(10.05 M) causes a marked decrease in the yields of all hydrolysis products derived from la and IC, except the rearrangement products ...