Reduction of chloroacetonitrile in DMF or MeCN at a Hg or a glassy carbon electrode involves a protonation reaction between the electrogenerated carbanion NCCH2- and the starting halide. Such a self-protonation reaction can be avoided by adding good carbanion scavengers such as proton donors or CO2. Reduction of the halide in CO2-saturated solvents yields cyanoacetic acid. This process was investigated under various experimental conditions. The best results, in both solvents, were obtained when an undivided cell with aluminum sacrificial anode was used. The yields of the acid, under such conditions, were 73% and 93% in DMF and MeCN, respectively.
Electrochemical Reduction and Carboxylation of Chloroacetonitrile
AHMED ISSE, ABDIRISAK;GENNARO, ARMANDO
2002
Abstract
Reduction of chloroacetonitrile in DMF or MeCN at a Hg or a glassy carbon electrode involves a protonation reaction between the electrogenerated carbanion NCCH2- and the starting halide. Such a self-protonation reaction can be avoided by adding good carbanion scavengers such as proton donors or CO2. Reduction of the halide in CO2-saturated solvents yields cyanoacetic acid. This process was investigated under various experimental conditions. The best results, in both solvents, were obtained when an undivided cell with aluminum sacrificial anode was used. The yields of the acid, under such conditions, were 73% and 93% in DMF and MeCN, respectively.Pubblicazioni consigliate
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