Abstract
Abstract The reactivity of the carbanion (CH2CO2Et)−, obtained from CH2(Br)CO2Et (I) by means of electrochemical reduction, on substrates such as CH2(Br)CH2CO2Et (II), CH2(Br)(CH2)2CO2Et (III) and CH2(Br)(CH2) 3CO2Me (IV), was studied in dimethylformamide solutions by means of polarography, cyclic voltammetry and coulometry at mercury and vitreous carbon electrodes. Evidence was found for coupling (diethyl glutarate (CH2)3(CO2Et)2 and diethyl adipate (CH2)4(CO2Et)2) and elimination reaction (ethyl acrylate CH2CHCO2Et and ethyl cyclopropancarboxylate CH 2 CH 2 C HCO2Et) compounds. In addition, the electrochemical reduction of the single esters (I)–(IV) was reported. The dependence of the percentage ratio among the various products obtained on the potential, the proton donor presence and the nature of the ester were investigated.
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