Canadian Journal of Chemistry

The mechanisam of electrochemical reduction of N-haloamides in acetonitrile: trapping of intermediate amide anions and father-son protonation

D Bérubé, J Lessard

Index: Berube, Denis; Lessard, Jean Canadian Journal of Chemistry, 1982 , vol. 60, p. 1127 - 1142

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Citation Number: 14

Abstract

The electrochemical reduction of N-haloamides (ZCONRX) in acetonitrile involves two consecutive one-electron transfers and generates the amide anion. Attempts to trap the intermediate amidyl radical resulting from the first electron transfer were unsuccessful. In the case of the N-halo-N-hydroamides (R= H), the amide anion formed at the electrode abstracts a proton from an incoming N-halo-N-hydroamide molecule to give the parent amide and ...