ELECTROCHEMICAL DEALKYLATION OF ALIPHATIC AMINES

The anodic oxidation of tertiary aliphatic amines in nonaqueous systems has been studied, using tri-n-propylamine in acetonitrile as a model. The reaction causes dealkylation to produce secondary amine and aldehyde. The reaction product contains unreactive tertiary and secondary amine salts in a 2:1 ratio. When water is rigorously excluded, elemental nitrogen is a major product. The investigation included 12 amines; effect of unsymmetrical substitution on the dealkylation was studied. Solvents used were tetrahydrofuran, dimethyl sulfoxide, water, ethanol-water, methanol, and 1,2-dimethoxyethane. © 1969, American Chemical Society. All rights reserved.