One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Symmetrical bisamides of ethylene diamine of type ArCONHCH 2 CH 2 NHCOAr undergo anodic C–C bond cleavage in acetonitrile–LiClO 4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem -bisamides of type ArCONHCH 2 NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem -bisamides of type ArCONHCH 2 NHCOAr and MeCONHCH 2 NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH 2, and ArCN).