Reduction by dissolving metals. Part XVI. Reactions of some aromatic amines with metal–ammonia solutions

Abstract

The reduction in liquid ammonia, preferably by lithium and t-pentyl alcohol, of some NN-dimethylanilines and some N-arylmorpholines has been examined. The products normally isolated are conjugated cyclohexadienamines, except in the case of ortho-substituted amines, from which stable unconjugated cyclohexadienamines can be obtained. In some other cases, with sufficient care, unconjugated dienamines can be isolated, but they undergo ready thermal conjugation at temperatures above ca. 30°. The morpholine derivatives are easier to handle and more stable than the NN-dimethylamino-derivatives. The conjugated and unconjugated dienamines have characteristic u.v., i.r., and n.m.r. spectra.