Electrochemical studies on haloamides. Part 3. Haloacetamides and halo-acetohydroxamates

Abstract

The electrochemical reduction of haloacetamides and acetohydroxamates 1 and 2 at a cathode in DMF–0.1 mol dm^–3 TEAP (tetraethylammonium perchlorate)solution has been investigated.

The reduction leads to the corresponding dehalogenated products together with cyclic dimers, arising from follow-up reactions of the conjugated base of the starting compound. The same type of products, but in quite different yield, are formed when ethyl isobutyrate anion is electrogenerated in the presence of chloro derivatives 1. The reactivity of the substrates, and in particular the structure of the dimers, primarily depends on the nature of the substituent at the amide nitrogen. Possible reaction pathways leading to the products are suggested.