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

Abstract

The reactions of acyclic and cyclic aliphatic amines with 1,2,3,4-tetrachloro-5,6-dinitrobenzene have been investigated under phase-transfer conditions (toluene–water in the presence of Aliquat 336). In comparison with the corresponding reactions in toluene alone as solvent, overall reactivity was increased, and there was an enhanced preference for chlorine rather than nitro-group displacement. An explanation for this is advanced.