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Toshio Koizumi, Toshio Fuchigami, Zaghloul El-Shahat Kandeel, Norio Sato, Tsutomu Nonaka, Reaction Mechanism of Cathodic Crossed Coupling of Acetone with Unsaturated Compounds in Acidic Solution, Bulletin of the Chemical Society of Japan, Volume 59, Issue 3, March 1986, Pages 757–762, https://doi.org/10.1246/bcsj.59.757
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Abstract
It was confirmed that the cathodic crossed coupling of acetone with unsaturated compounds in aqueous sulfuric acid could proceed smoothly, when the compounds which had radical-acceptable double bonds and were adsorbed on a mercury cathode were used. From this fact, it was concluded that the coupling occurs via the addition of a radical intermediate formed by the one-electron reduction of acetone to the double bonds on the cathode surface. Possibility of the addition of an anionic intermediate derived from acetone was excluded by no occurrence of the coupling of acetone with a polar acetylenic triple bond compound adsorbed on the cathode.