Reaction of Mono-, Di-, and Trichloronitrobenzenes with N-Methyl Substituted Cyclic Tertiary Amines under High Pressure

Article abstract of DOI:10.1246/bcsj.68.2717

The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylpyrrolidine under high pressure gave products of demethylation and ring-opening through a quaternary pyrrolidinium chloride intermediate formed by the S_NAr reaction.On the other hand, the reactions with 1-methylpiperidine and 4-methylmorpholine gave only demethylation products.The selectivities of the resctions of 1-methylpyrrolidine with these chloronitrobenzenes were found to be effected by the neighboring substituent to the pyrrolidinium group.