Some Trithiocarbonate Derivatives of Carbohydrates

Abstract

ETHYLENE oxide (I) and its simple analogues react with carbon disulphide and potassium hydroxide in methyl alcoholic solution to give cyclic compounds, containing three atoms of sulphur, which are termed trithiocarbonates. Culvenor, Davies and Pausacker1 described the transformation of ethylene oxide into ethylene trithiocarbonate (II), and of cyclohexene oxide into cyclohexene trithiocarbonate. Furthermore, although this transformation has not yet been carried out, these compounds should readily undergo reductive desulphurizationwith Kaney nickel, according to the method of Bougault, Cattelain and Chabrier2, and afford ethane and cyclohexane. It occurred to us that the exploitation of these two reactions in the carbohydrate series might lead to a method of introducing two vicinal deoxy groups into sugar molecules, which might be of value considering the importance now assumed by deoxysugars in modern carbohydrate chemistry.

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References

  1. 1

    Culvenor, C. C. G., Davies, W., and Pausacker, K. H., J. Chem. Soc., 1050 (1946).

  2. 2

    Bougault, J., Cattelain, E., and Chabrier, P., C.R. Acad. Sci., Paris, 208, 657 (1939).

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  3. 3

    Haworth, W. N., and Porter, C. R., J. Chem. Soc., 2796 (1929).

  4. 4

    Bladon, P., and Owen, L. N., J. Chem. Soc., 598 (1950).

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MCSWEENEY, G., WIGGINS, L. Some Trithiocarbonate Derivatives of Carbohydrates. Nature 168, 874–875 (1951). https://doi.org/10.1038/168874b0

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