No 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.

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ChemInform Abstract The substitution reactions of the N,N-dimethyl analogue of (I) with prim. amines such as (VI) show that benzylamine (VIa) is more reactive than aromatic prim. amines such as (VIb) but less reactive than aliphatic prim. ones. The dependence of substitution on the conformation of nucleophilic amines is discussed.