Anodic oxidation of amines. Part II. Electrochemical dealkylation of aliphatic tertiary amines

Abstract

NN-Dimethyl tertiary amines undergo oxidative dealkylation on anodic oxidation in aqueous alkaline solution at glassy-carbon electrode, and the major products are secondary amines and the appropriate aldehydes. On prolonged electrolysis the secondary amines produced undergo partial oxidative dealkylation to give primary amines and the appropriate aldehydes. The relative amount of dealkylation in unsymmetrical amines is predominantly governed by the acidity and the number of α-protons, but is also affected by the ease of oxidation of the radical R¹₂NCHR². Decarboxylation of the cation radical Me₂N + CH₂CO₂– is involved in the anodic oxidation of NN-dimethylglycine.