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

doi:10.1039/P29960002623

Paper

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

Published 1996 · D. Rondeau, E. Raoult, A. Tallec

Journal of The Chemical Society-perkin Transactions 1

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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.

Study Snapshot

Electroreduction of tetraactivated 4H-thiopyrans selectively produces diastereoisomers of dihydrothiopyrans, with their conformations determined by X-ray crystallography and 1H NMR spectroscopy.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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Electrochemical reduction of 2-phenyl-6H-1,3-thiazines at a mercury cathode in acetate buffer + ethanol (1:1) leads to various products, compared to chemical reductions with NaBH3CN and LiAlH4 respectively.

Citations

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Thiopyrans and their benzo derivatives have potential applications in biological, pharmaceutical, and materials chemistry.

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Electrochemistry of heterocycles enables the formation of double bonds, functionalization of heterocycles, and the synthesis of new compounds.

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Electrochemical reduction of pyridazines with electron-withdrawing groups can produce activated pyrroles, depending on ring substitution.

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