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Electrochemically Initiated Hydrocyanomethylation of N-Heteroaryl-Substituted Azomethines

✍ Scribed by Windeck, Anne-Kathrin ;Hess, Ulrich ;Steckhan, Eberhard ;Reck, Günter

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 588 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960920

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✦ Synopsis

Abstract

The acetonitrile anion (1‐), generated by electrochemical initiation and chemical regeneration, may be used as cyanomethylation reagent for C,N double bond structures, e.g. for hydrocyanomethylation of π‐deficient N‐heteroaryl‐substituted Schiff bases (2–12) yielding the β‐aminonitriles (2a–12a). The synthesis is initiated by deprotonation of acetonitrile (1) to 1^−^ by cathodically generated azomethine radical anions (2^−·^–12^−·^) followed by nucleophilic reaction of 1^−^ with 2–12 up to its complete consumption, in a cyclic self‐reproducing process of 1^−^. Besides 2a–12a, 3,4‐heteroaryl‐substituted 4‐amino‐3‐butenonitriles and 1,3‐heteroaryl‐substituted 1,3‐diaminoisobutyronitiles are formed in the course of a nearly currentless reaction.

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