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- ...