Aromatic nucleophilic substitution reactions of 1-dialkylamino-2,4-dinitronaphthalenes with various amines in dimethyl sulphoxide. Part 26.

Abstract

The dialkylamino group (e.g., dimethyl-, diethyl-, and N-methylbutyl-amino, piperidino, and pyrrolidino) of 1-dialkylamino-2,4-dinitronaphthalenes is readily replaced by primary alkylamines in dimethyl sulphoxide. However, substitution does not occur for secondary alkylamines except in the case of pyrrolidine. Aromatic primary amines (p-methoxy-, p-methyl-, and p-nitro-anilines and aniline) are less reactive than aliphatic primary amines, probably owing to their nucleophilicity and bulkiness. Benzylamine is more reactive than aromatic primary amines, but less reactive than aliphatic primary amines. Dependence of substitution on the conformation of nucleophilic amines is discussed.