Kinetics of the reactions of piperidine, n-butylamine, morpholine, and benzylamine with 2,4-dinitrophenyl phenyl ether

Abstract

The kinetics of the reactions designated in the title have been studied as a function of amine concentration in acetonitrile, dimethyl sulphoxide, and (for piperidine and n-butylamine only) methanol. In all the solvents studied, the reactions of the secondary amines are base-catalysed : those of the primary amines are not. The results are interpreted in terms of the generally accepted mechanism of nucleophilic aromatic substitution.