REACTION OF MONOCHLORONITROBENZENES, DICHLORONITROBENZENES, AND TRICHLORONITROBENZENES WITH N-METHYL SUBSTITUTED CYCLIC TERTIARY-AMINES UNDER HIGH-PRESSURE

The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylp yrrolidine under high pressure gave products of demethylation and ring -opening through a quaternary pyrrolidinium chloride intermediate form ed by the SNAr reaction. On the other hand, the reactions with 1-methy lpiperidine and 4-methylmorpholine gave only demethylation products. T he selectivities of the reactions of 1-methylpyrrolidine with these ch loronitrobenzenes were found to be effected by the neighboring substit uent to the pyrrolidinium group.