NUCLEOPHILIC-SUBSTITUTION REACTION OF 2,3,5,6-TETRACHLORONITROBENZENEWITH PRIMARY AND SECONDARY-AMINES UNDER HIGH-PRESSURE

Nucleophilic substitution of 2,3,5,6-tetrachloronitrobenzene with seco ndary amines such as morpholine, piperidine, pyrrolidine, diethylamine , and ethylmethylamine, and primary amines such as aniline, benzylamin e, butylamine, isobutylamine, s-butylamine, and t-butylamine, under hi gh pressure of 0.6 GPa at 50 degrees C for 1-40 h in tetrahydrofuran g ave nitro group substitution products together with ortho-mono-, meta- mono-, ortho-ortho-, and ortho-meta-dichloro substitution products. Th e ratio of these products depends on the bulkiness and amount of amine s and the reaction conditions. The selectivity of the nitro group subs titution and chlorine substitution depends mainly on the bulkiness of amines.