Utilisation en synthese du cation iminium genere in situ par oxydation electrochimique d'amines tertiaires

The electrochemical oxidation in acetonitrile of aliphatic amines (ACH₃) in presence of a non-nucleophilic base (2,4,6-collidine) and of compounds containing weakly-activated hydrogens (RH) such as diethyl phosphonate and diethyl malonate gives the substituted derivatives ACH₂R. These compounds result from the addition of the anion R^? to the iminium cation ACH₂⁺. Such a reaction is obtained with tribenzylamine and N,N-dimethyl-p-toluidine. Moreover (CH₃)₂NCH₂-CH(CO₂C₂H₅)₂ is deaminated and gives by successive Michael reactions other substituted malonates which also react with the iminium cation (CH₃)2N⁺CH₂.