N-alkyl-N-cyclopropylanilines as mechanistic probes in the nitrosation of N, N-dialkyl aromatic amines

RN Loeppky, S Elomari

Index: Loeppky, Richard N.; Elomari, Saleh Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 96 - 103

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Citation Number: 44

Abstract

A group of N-cyclopropyl-N-alkylanilines has been synthesized, and their reaction with nitrous acid in aqueous acetic acid at 0° C was examined. All compounds reacted rapidly to produce the corresponding N-alkyl-N-nitrosoaniline by specific cleavage of the cyclopropyl group from the nitrogen. The transformations were unaffected by the nature of the alkyl substituent (Me, Et, i Pr, Bn). The reaction of 4-chloro-N-2-phenylcyclopropyl-N- ...