Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Acetylenic sulfones and sulfoxides

Communication 1. Synthesis and polarographic study of ethynylalkyl sulfones


  1. 1.

    A preparative method of synthesizingethynylalkyl sulfones RSO2C≡CH (R=CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, t-C4H9) was developed, and their physicochemical characteristics were given.

  2. 2.

    In the electrochemical reduction of ethynylalkyl sulfones, there is a stepwise hydrogenation of the triple bond to a double bond and then to a saturated bond; as a result of the activating effect of the sulfonyl group, the first step is substantially facilitated.

  3. 3.

    For ethynylalkyl sulfones with unbranched radicals, the half-wave potentials E1/2 are correlated with σ* constants of the alkyls, while steric effects are manifested for compounds with branched substituents.

  4. 4.

    The values found for the constantρ show that inductive effects of the alkyl substituents have little effect on the reactivity of the highly electrophilic triple bond of ethynylalkyl sulfones: in vinylalkyl sulfones the inductive influence of alkyl radicals on E1/2 is more strongly manifested.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    M. K. Polievktov, S. G. Mairanovskii, V. I. Laba, V. I. Snegotskii, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 687 (1968).

  2. 2.

    E. N. Prilezhaeva, Dissertation [in Russian], Moscow (1963).

  3. 3.

    R. N. Ring, G. C. Tesoro, and D. R. Moore, J. Organ. Chem.,32, 1091 (1967).

  4. 4.

    C. C. Price and S. Oae, Sulfur Bonding, Ronald Press Comp., New York (1962), pp. 61–129; H. A. Bent, in: Organic Sulfur Compounds, N. Kharasch and C. Y. Meyers (editors), Vol.2, Pergamon Press (1966), p. 1.

  5. 5.

    G. Cilento, Chem. Rev.,60, 165 (1960).

  6. 6.

    US Patent No. 2634202; Chem. Abstrs.,125, 5613 (1954).

  7. 7.

    W. E. Parham and P. L. Stright, J. Amer. Chem. Soc.,78, 4783 (1956); G. Pourcelot, P. Cadiot, and A. Willemart, Compt. Rend.,252, 1630 (1961); C. J. M. Stirling, J. Chem. Soc. Suppl., 1., 5856 (1964); R. C. Pink, R. Spratt, and C. J. M. Stirling, J. Chem. Soc., 5714 (1965).

  8. 8.

    W. E. Truce and D. G. Brady, J. Organ. Chem.,31, 3543 (1966).

  9. 9.

    C. H. McMullen and C. J. M. Stirling, J. Chem. Soc. (B), 1217 (1966).

  10. 10.

    L. Di Nunno, G. Modena, and G. Scorrano, J. Chem. Soc. (B), 1186 (1966).

  11. 11.

    S. T. McDowell and C. J. M. Stirling, J. Chem. Soc. (B), 351 (1967).

  12. 12.

    J. F. Arens, Advances in Organic Chemistry: Methods and Results, Vol.2, Interscience Publishers, Inc., New York (1960), p. 199.

  13. 13.

    L. Maioli and G. Modena, Ricerca Sci.,29, 1931 (1959); Chem. Abstrs.,54, 10928h (1960).

  14. 14.

    M. F. Shostakovskii, E. N. Prilezhaeva, and N. I. Uvarova, Izv. AN SSSR, Otd. Khim. N., 906 (1955).

  15. 15.

    J. E. Arens and T. Doornbos, Recueil Trav. Chim.,75, 481 (1956).

  16. 16.

    K. Bowden, I. M. Heilbron, E. R. H, Jones, and B. C. L. Weedon, J. Chem. Soc., 39 (1946).

  17. 17.

    B. A. Arbuzov and E. A. Berdnikov, Dokl. Akad. Nauk SSSR,171, 860 (1966).

  18. 18.

    A. A. Pozdeeva, S. G. Mairanovskii, and L. K. Gladkova, Élektrokhimiya,3, 1127 (1967).

  19. 19.

    V. G. Ostroverkhov and A. E. Shilov, Ukr. Khim. Zh.,22, 590, 743 (1956);23, 615 (1957);27, 209 (1961); S. N. Bondarev and A. A. Petrov, Zh. Organ. Khim.,4, 27 (1968).

  20. 20.

    H. A. Laitinen and S. Wawzonek, J. Amer. Chem. Soc.,64, 1765 (1942).

  21. 21.

    I. Rosenthal, J. R. Hayes, A. J. Martin, and P. J. Elving, J. Amer. Chem. Soc.,80, 3050 (1958).

  22. 22.

    G. Capobianco, E. Vianello, and G. Giacometti, Gazz. Chim. Ital.,97, 243 (1967).

  23. 23.

    S. R. Missan, E. I. Becker, and L. Meites, J. Amer. Chem. Soc.,83, 58 (1961).

  24. 24.

    V. P. Gul'tyai, S. G. Mairanovskii, N. K. Lisitsina, and M. V. Mavrov, Izv. Akad. Nauk SSSR, Ser. Khim., 1655 (1968).

  25. 25.

    G. A. Tedoradze and A. B. Érshler, Uspekhi Khimii,34, 1866 (1965).

  26. 26.

    B. Kastening and L. Holleck, Talanta,12, 1259 (1965).

Download references

Author information

Additional information

For a preliminary Communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2149–2156, October, 1969.

The NMR spectra were obtained by V. S. Bogdanov, and the IR spectra by E. D. Lubuzh, to whom the authors would like to express their gratitude.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Laba, V.I., Polievktov, M.K., Prilezhaeva, E.N. et al. Acetylenic sulfones and sulfoxides. Russ Chem Bull 18, 2004–2010 (1969).

Download citation


  • Hydrogenation
  • Sulfone
  • Double Bond
  • Sulfoxide
  • Alkyl Radical