Darstellung, physikalische Eigenschaften und Kristallstrukturen von Mono-, Di- und Trichlor-2,4,6-tris(dialkylamino)benzolen (Aminobenzole ; 22)

Abstract

Mono-, di- and trichlorotris(dialkylamino)benzenes 2,3, and 4 are prepared selectively by chlorination of triaminobenzenes 1 with one, two, or three equivalents of N-chlorosuccinimide, resp., in tetrachloromethane. From spectroscopic data it is deduced that the introduction of chloro substituents into symmetrical triaminobenzenes 1 causes a severe steric hindrance for the dialkylamino groups without disturbing the aromatic π system. X-ray structural analyses of the trichlorotriamino compounds 4a and 4c confirm the spectroscopic interpretation. Among the trichloro compounds 4a - d only for 4c the anodic oxidation is reversible.