Surprising electrooxidation of propargyl alcohol to (Z)-3-(2-propynoxy)-2- propenoic acid at a NiOOH electrode in alkaline medium

The electrooxidation of the unsaturated propargyl alcohol has been explored on NiOOH electrodes in alkaline solution. Cyclic voltammetry, chronoamperometry and electrolyses were performed for the electrochemical response of propargyl alcohol. The identification and quantification of the final products from the electrolyses have been carried out. No evidence for the formation of propiolic acid has been found, however, a new product, (Z)-3-(2-propynoxy)-2-propenoic acid, was obtained. The stereochemistry of the product could be ascertained by ¹H NMR spectroscopy. A tentative mechanism for the formation of (Z)-3-(2-propynoxy)-2-propenoic acid has been developed.