Kinetics of the reactions of aniline and 2,2,2-trifluoroethylamine with 1,3,5-trinitrobenzene in dimethyl sulphoxide and acetonitrile, and of 2,2,2-trifluoroethylamine with 1-fluoro- and 1-chloro-2,4-dinitrobenzenes in these solvents

Abstract

Meisenheimer complex formation between 1,3,5-trinitrobenzene (TNB) and the primary amines aniline and 2,2,2-trifluoroethylamine (TFE) has been studied in dimethyl sulphoxide and acetonitrile. The reaction with aniline is catalysed in both solvents by 1,4-diazabicyclo[2.2.2]octane (DABCO). With TFE, catalysis by both TFE and DABCO was observed in acetonitrile, but not in dimethyl sulphoxide. The reactions of TFE with 1-fluoro- and 1-chloro-2,4-dinitrobenzenes are not base catalysed in dimethyl sulphoxide or acetonitrile.