Reduction of aliphatic bromoesters

Mechanistic investigation of the iron-mediated electrochemical formation of β-hydroxyesters from α-haloesters and carbonyl compounds

“…It must be pointed out that methyl 2-bromopropanoate is reducible at À1.8 V under the same conditions (electrode, scan rate, etc.). On the basis of our results and of those reported by Zeuli and Inesi dealing with the indirect and direct reduction of bromoesters, the reduction of a-haloesters therefore leads to the corresponding radical-anion along with the regeneration of Fe II [26][27][28][29][30]. The radical-anion then undergoes a cleavage affording an ester radical and a free halide ion.…”

“…The reactivity of carbanions of the type (CH 2 CO 2 Et) À , obtained by electrochemical reduction of CH 2 (Br)CO 2 Et, has been widely studied by means of cyclic voltammetry and coulometry [30]. Evidence was found for coupling reactions leading to the formation of hydrogenated ester and dimeric products.…”

Direct electrochemical reduction of a bromo-propargyloxy ester at vitreous carbon cathodes in dimethylformamide

“…Inesi et al [6] probed the direct reduction of several bromoesters at mercury and glassy carbon cathodes and reported the formation of the corresponding hydrogenated esters as well as unsaturated products that arise via elimination of a molecule of hydrogen bromide. In addition, a-and b-bromoesters were observed to afford dimeric products, and reduction of the former family of compounds was shown to proceed via both unbrominated and brominated carbanions as intermediates [7]. In an investigation of the direct reduction of a; c-dibromoesters at mercury, Giomini et al [8] concluded that cyclic products can be formed via carbanion intermediates.…”