Electrochemical reduction of 2-bromo-carboxamides. Self-protonation mechanism and reaction with dimethylformamide

…, E Vianello, G Cavicchioni, F D'Angeli

Index: Maran, Flavio; Vianello, Elio; Cavicchioni, Giorgio; D'Angeli, Ferruccio Journal of the Chemical Society, Chemical Communications, 1985 , # 10 p. 660

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Abstract

Electrochemical reduction of 2-bromo-carboxamides involves self-protonation of the electrogenerated bases and affords, among other products, cyclo-adducts incorporating a dimethylformamide unit. ... Base-promoted self- and cross-cyclocondensation of 2-bromo- carboxamides BrCR3R4CONRlR2 occur with useful regioselectivity , affording various heterocyclic products. 1 Some mechanistic pathways are being investigated through a6 initio calculations,2 but we thought it would ...