The electrochemical behaviour of carboxamides bearing several types of electrophoric substituents has been investigated from both mechanistic and synthetic point of view. The formation of anionic intermediates through electrodic cleavage of the electrophoric C - Hal or N- S bonds or following acid-base reaction with electrogenerated bases has been established. The reactivity of these intermediates strictly depends on the structure of the amide. In particular, the presence of leaving groups allows the synthesis of unsaturated or cyclic derivatives, according to other structural features. High yielding procedures for the synthesis of lactams, in particular functionalized β-lactams, and for the selective deblocking of protective groups have been developed. Concerning yield, selectivity, reaction conditions, generality of substrate and scope, these electrochemical methodologies can be regarded as competitive with or better than correspondent traditional chemical syntheses.
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