UTILISATION EN SYNTHESE DU CATION IMINIUM GENERE IN SITU PAR OXYDATION ELECTROCHIMIQUE D'AMINES TERTIAIRES

Article abstract of DOI:10.1016/S0040-4020(01)97987-6

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(1-) to the iminium cation ACH2(1+).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(1+)=CH2.