Reaction of 2,4-dinitrophenyl phenyl ether with morpholine in dimethyl sulphoxide, acetonitrile, tetrahydrofuran, and ethyl acetate and of 1-chloro-2,4-dinitrobenzene with morpholine in ethyl acetate

Abstract

The reaction of morpholine with 2,4-dinitrophenyl phenyl ether is base-catalysed in all the solvents investigated. The values of k₃/k₂ provide information about the mechanism of the uncatalysed decomposition of the intermediate formed in nucleophilic aromatic substitution in solvents of high dielectric constant.

The reaction of morpholine with 1-chloro-2,4-dinitrobenzene in ethyl acetate is not base-catalysed. Comments are made on the mechanism of base-catalysed nucleophilic aromatic substitution in solvents of low dielectric constant and basicity.