| Abstract: | Electrocatalyzed Cyanomethylation of Azomethines: A New Synthesis for β-Aminonitriles Certain Schiff-bases ( 2–7 ) react in acetonitrile ( 1 ) at a Hg-cathode in a new electrocatalyzed cyanomethylation method in good yields without side-products to β-aminonitriles ( 2a–7a ). The synthesis is initiated by an electrochemical deprotonation of 1 by azomethine-radical anions in catalytical amount to acetonitril anions (B−). During nucleophilic reaction of B− with 2–7 up to its complete consumption, the cyanomethylation synthon B− is regenerated in a cyclic, self-reproducing process. Quantum chemical calculation in context with cyanomethylation product analysis permit mechanistical insights and exact prediction of suitable azomethines and coupling position for B−. |
