Collect. Czech. Chem. Commun. 1981, 46, 498-502

Electrochemical reduction of para-substituted 2-acyl-5-phenylfuranes in dimethylformamide

Jozef Černáka, František Tomanoviča, Andrej Staškoa, Anna Fedosyevna Oleinikovab and Jaroslav Kováča

a Department of Chemical Technology, Slovak Institute of Technology, 880 37 Bratislava, Czechoslovakia
b Vsesoyuznyi Nauchnoissledovatelskii Khimiko-Farmaceuticheskii Institut Imeni C. Ordzhonikidze, Moscow, USSR


para Substituted chloro, bromo, and nitro derivatives of 2-acyl-5-phenylfurane are reduced polarographically in a one-electron wave to the corresponding anion radicals, which were studied by the EPR method. The reduction of nitro derivatives, studied by the Kalousek switch, is reversible and leads to a stable anion radical with an unpaired electron center on the nitrogen nucleus; the reduction of the halogen derivatives is only partly reversible and leads to unstable ketyl radicals. The bromo derivatives give polarographic maxima typical for concurrent reactions.