Issue 12, 1996

Electrochemical access to functionalized dihydrothiopyran derivatives. Part 1: electroreduction of tetraactivated 4H-thiopyrans

Abstract

Electroreduction of tetraactivated 4H-thiopyrans leads selectively to diastereoisomers of dihydrothiopyrans. The relative percentages depend on the experimental conditions (electrolysis in sulfuric medium, ammoniacal buffer). The preferred conformations of the end-products are determined in solid state by X-ray crystallography and in solution by 1H NMR spectroscopy, then compared with molecular modelling results. The relative conformations of the diastereoisomers and their ratio are established by 1H NMR spectroscopy.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1996, 2623-2629

Electrochemical access to functionalized dihydrothiopyran derivatives. Part 1: electroreduction of tetraactivated 4H-thiopyrans

D. Rondeau, E. Raoult, A. Tallec, S. Sinbandhit, L. Toupet, A. Imberty and J. P. Pradère, J. Chem. Soc., Perkin Trans. 2, 1996, 2623 DOI: 10.1039/P29960002623

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