Mechanism of the Electrochemical Reduction of Enolized 1,3-Diketones

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Abstract
A mechanism for the electrochemical reduction of 1,3‐diphenyl‐1,3‐propanedione (1) and other enolized 1,3‐diketones in aprotic solvents has been developed on the basis of cyclic voltammetric studies. The over‐all reaction is a 0.5‐electron process producing the enolate anion of the 1,3‐diketone and the dimeric pinacol. The central feature of the mechanism is a one‐electron reversible reduction to the radical anion of the 1,3‐diketone followed by a fast, reversible proton transfer from unreacted diketone to the radical anion forming enolate and a neutral radical. The neutral radicals then undergo rapid coupling reactions. The electrochemical behavior of 1,3‐diketones existing in the diketo form is contrasted with the above scheme.

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