Electrochemical Synthesis of Keto and Enol Forms of Tetraketones of the Type 3,4-Diaroyl-2,5-hexanedione by Oxidative Dimerization of Aroylacetones

Abstract

Tetraketones of the type 3,4-diaroyl-2,5-hexanedione: Ar = CsH;-, p-CHs-CsH4-, 3,4-(CHsh-CsHs-, p-CHaO-CsH4-, p- Cl-CsH4-, p-Br-C6H4- and 2-C4H3S- were prepared in good yield by oxidative anodic dimerization of aroylacetones. Electrochemical oxidation was carried out at constant current (4-5 A) in cylindrical cell without diaphragm with Pt-gauze anode and Ni-cathode. Depending on the method used (A or B) and depending on the properties of the electrolysed aroylacetones, dimer-products were isolated as stable keto or enol tautomers. Electrolysis in 80°/o aqueous methanol (Method A) gave keto or enol tautomers, while electrolysis in absolute methanol (Method B) yielded only enol tautomers

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