Journal of Organic Chemistry p. 1189 - 1196 (1980)
Update date:2022-08-04
Topics:
Degrand, Chantal
Compagnon, Paul-Louis
Belot, Gerard
Jacquin, Dominique
The one-step synthesis of cyclic compounds is achieved in a few cases by electroreduction of unsaturated compounds in DMF, at a mercury pool cathode, in the presence of a more difficulty reducible dielectrophile.Unsaturated compounds include activated olefins, aromatic Schiff bases, ketones, and azo, nitroso, and nitro compounds.Four dielectrophiles are used; they are tri- or tetramethylene bromide, succinyl chloride, and 4-bromobutyryl chloride.The electrochemical synthesis of derivatives of cyclohexane, piperidine, pyrrolidine, hexahydropyridazine, tetrahydropyridazinone, tetrahydropyridazinedione, tetrahydrooxazine, isoxazolidine, and spirolactone can be succesfully performed.Their yields range from 8 to 78percent depending on competitive reactions.Results of chemical reduction by alkali metals and electrochemical reduction are compared.
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