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Aminobenzole, 22. Darstellung, physikalische Eigenschaften und Kristallstrukturen von Mono‐, Di‐ und Trichlor‐2,4,6‐tris(dialkylamino)benzolen
Author(s) -
Effenberger Franz,
Mündl Gabriele
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250139
Subject(s) - chemistry , steric effects , crystal structure , tris , medicinal chemistry , stereochemistry , crystallography , biochemistry
Aminobenzenes, 22. — Synthesis, Physical Properties, and Crystal Structures of Mono‐, Di‐, and Trichloro‐2,4,6‐tris‐(dialkylamino)benzenes 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.