The kinetics of the reactions of aniline with 1-fluoro- and 1-chloro-2,4-dinitrobenzenes in dimethyl sulphoxide, dimethylformamide, acetonitrile, and nitromethane

Abstract

The reaction of aniline with 1-fluoro-2,4-dinitrobenzene is base catalysed in the solvents dimethylformamide, acetonitrile, and nitromethane, but not in dimethyl sulphoxide. The reaction with 1-chloro-2,4-dinitrobenzene is not base catalysed in any of these solvents. The results provide information about the mechanism of the uncatalysed decomposition of the intermediate formed in nucleophilic aromatic substitution in solvents of high dielectric constant.