One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical <i>gem</i>-Bisamides of Methylene Diamine
作者:Tatiana Golub、Gui-yuan Dou、Cheng-chu Zeng、James Y. Becker
DOI:10.1021/acs.orglett.9b02917
日期:2019.10.4
Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor
ArCONHCH2CH2NHCOAr型乙二胺的对称双酰胺在受控电势下在乙腈-LiClO4中进行阳极CC键裂解。电生成的碳正离子中间体与溶剂乙腈反应,通过一锅法反应提供ArCONHCH2NHCOMe类型的不对称的宝石双酰胺。后一种产品的产率中等(高达60%)。其他次要产品涉及ArCONHCH2NHCOAr和MeCONHCH2NHCOMe类型的两种对称的宝石双酰胺和片段化产品(例如ArCONHCHO,ArCONH2和ArCN)。