RATE INCREASE IN CONSECUTIVE NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTIONS OF TRICHLOROTRINITROBENZENE - THE SYNTHESIS OF 1-(ALKYLAMINO)-3,5-DICHLORO-2,4,6-TRINITROBENZENES

The title compounds are formed by the nucleophilic aromatic substituti on reaction between sym-trichlorotrinitrobenzene and amines. The yield s and relative rates of formation depend critically on the degree of a lkylation of the nucleophile. Contrary to the usual behavior, the intr oduction of a second and third donor is facilitated in the case of amm onia and monoalkylamines, while this is not the case for secondary ami nes. This behavior is rationalized on the basis of intramolecular hydr ogen bonding and substantiated by an X-ray analysis of 3,5-dichloro-2, 4,6-trinitroaniline.