One-step Synthesis of Cyclic Compounds by Electrochemical Reduction of Unsaturated Compounds in the Presence of Dielectrophiles

Article abstract of DOI:10.1021/jo01295a004

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.