Electrochemical reduction of ketones mediated by (dimethylpyrrolidinio) mercury. Reductive cyclization of unsaturated ketones and redox catalysis studies

…, TJ Mahachi, E Kariv-Miller

Index: Swartz, James E.; Mahachi, Tendai J.; Kariv-Miller, Essie Journal of the American Chemical Society, 1988 , vol. 110, p. 3622 - 3628

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Citation Number: 33

Abstract

Abstract: The mechanism of dimethylpyrrolidinium (DMP') mediation of the reductive cyclization of 6-hepten-2-one at a mercury electrode was studied. The initial step of the reduction involves formation of a solid composite,(DMP) Hg,, which then transfers an electron to the ketone, regenerating DMP+ and Hg'. The ketyl radical anion cyclizes to form a primary alkyl radical, which can either abstract a hydrogen atom from the solvent, ...