Journal fur Praktische Chemie - Chemiker-Zeitung p. 487 - 490 (1992)
Update date:2022-08-04
Topics:
Hess, U.
Raasch, A.-K.
Schulze, M.
Certain Schiff-bases (2-7) react in acetonitrile (1) at a Hg-cathode in a new electrocatalyzed cyanomethylation method in good yields without sideproducts 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-.
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