70526-01-1Relevant articles and documents
One-step Synthesis of Cyclic Compounds by Electrochemical Reduction of Unsaturated Compounds in the Presence of Dielectrophiles
Degrand, Chantal,Compagnon, Paul-Louis,Belot, Gerard,Jacquin, Dominique
, p. 1189 - 1196 (2007/10/02)
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.
