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Deuterium exchange in a number of 3-substituted sulfolanes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The NaOD-catalyzed isotopic exchange of hydrogen in the 2 position of 3-methoxysulfolane was investigated by PMR spectroscopy, and its pK a value was estimated to be 24.67. Increased acidity is characteristic for the methylene group of 3-hydroxysulfolane in the 2 position and the methylene group of 3,4-dimethoxysulfolanes in the 2 and 5 positions.

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Literature cited

  1. B. S. Thyagaraijan, Mechanisms of Reactions of Sulfur Compounds, Vol. 4 (1969), p. 115.

    Google Scholar 

  2. F. G. Bordwell, R. H. Ines, and E. C. Steiner, J. Amer. Chem. Soc., 89, 3905 (1967).

    Google Scholar 

  3. R. Radeglia, K. Edelmann, and G. Malewski, Monatsberichte, 11, 366 (1969).

    Google Scholar 

  4. T. É. Bezmenova, Yu. N. Usenko, L. F. Rekasheva, I. S. Lushnik and A. V. Misyura, Khim. Geterotsikl. Soedin., 767 (1972).

  5. N. M. Émanuel' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1969).

  6. T. H. Fife and T. C. Bruice, J. Phys. Chem., 65, 1079 (1961).

    Google Scholar 

  7. R. G. Pearson and R. L. Dillon, J. Amer. Chem. Soc., 75, 2439 (1953).

    Google Scholar 

  8. F. G. Bordwell, Abstracts of US-Japan Joint Seminar on Organosulfur Chemistry (1971).

  9. D. J. Cram, Fundamental Carbanion Chemistry Academic Press (1965).

  10. E. Koldin Fast Reactions in Solution [Russian translation], Mir, Moscow (1966), p. 275.

    Google Scholar 

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The compounds were obtained by R. A. Dorofeeva by the described methods.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1067–1071, August, 1975.

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Bezmenova, T.É., Kurlyand, D.I., Zaika, T.D. et al. Deuterium exchange in a number of 3-substituted sulfolanes. Chem Heterocycl Compd 11, 931–934 (1975). https://doi.org/10.1007/BF00470493

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  • DOI: https://doi.org/10.1007/BF00470493

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