Amination of Haloaromatics with Trichloramine-Aluminum Chloride. σ Substitution and Nucleophilic σ Substitution1, 2

P Kovacic, JF Gormish

Index: Kovacic,P.; Gormish,J.F. Journal of the American Chemical Society, 1966 , vol. 88, # 16 p. 3819 - 3824

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Citation Number: 3

Abstract

Abstract: Amination of halobenzenes (fluoro, chloro, and bromo) and halotoluenes (0-, m-, and p-fluoro, o-, m-, and p-chloro, and m-bromo) with trichloramine under Friedel-Crafts conditions was found to proceed by two main competing processes in yields of 20-41%. For example, the system, trichloramine-aluminum chloride-fluorobenzene, gave predominantly m-fluoroaniline and p-chloroaniline. We propose that the former is produced by a u- ...