Polyhalogenonitrobenzenes and derived compounds. Part 1. Reactions of 1,2,3,4-tetrachloro-5,6-dinitrobenzene with amines

Abstract

The relationship between amine structure and the nature of the products obtained in their reaction with 1,2,3,4-tetrachloro-5,6-dinitrobenzene has been investigated. Primary amines react by displacing a nitro group whereas acyclic secondary amines, in general, reacted by replacing a chlorine atom from a position ortho to a nitro group. The reactivity of cyclic secondary amines, e.g. piperidine was more variable. These results have been rationalised in terms of steric and electronic effects.