Russian Journal of Organic Chemistry

, Volume 41, Issue 7, pp 1023–1035 | Cite as

Reactions of 2-(α-Haloalkyl)thiiranes with Nucleophilic Reagents: IV. Alkylation of Sulfonamides with 2-Chloromethylthiirane. Synthesis and Properties of 3-(Arylamino)thietanes

  • V. V. Sokolov
  • A. N. Butkevich
  • V. N. Yuskovets
  • A. A. Tomashevskii
  • A. A. Potekhin


Alkylation of primary and secondary sulfonamides with 2-chloromethylthiirane in the presence of alkali gives the corresponding N-(thiiran-2-ylmethyl)- and/or N-(thietan-3-yl)sulfonamides. The selectivity of the process depends on the solvent: in water, thiirane-thietane rearrangement products are formed exclusively, while ethanol favors Ad-E reaction leading to thiiranylmethyl derivatives. A procedure has been proposed for the synthesis of 3-(arylamino)thietanes which undergo selective acylation at the nitrogen atom. The possibility for synthesizing analogous derivatives of thietane 1-oxide and thietane 1,1-dioxide is considered.


Nitrogen Sulfonamide Organic Chemistry Nitrogen Atom Alkylation 
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  1. 1.
    Tomashevskii, A.A., Sokolov, V.V., and Potekhin, A.A., Russ. J. Org. Chem., 2003, vol. 39, p. 226.CrossRefGoogle Scholar
  2. 2.
    Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Foundations of Organic Chemistry of Drugs), Moscow: Khimiya, 2001.Google Scholar
  3. 3.
    Adams, E.P., Ayad, K.N., Doyle, F.P., Holland, D.O., Hunter, W.H., Nayler, J.H.C., and Queen, A., J. Chem. Soc., 1960, vol. 82, p. 2665.CrossRefGoogle Scholar
  4. 4.
    Grammaticakis, G., Bull. Soc. Chim. Fr., 1953, p. 86.Google Scholar
  5. 5.
    Unterhalt, B. and Mollers, M., Arch. Pharm. (Weinheim), 1990, vol. 323, p. 317.Google Scholar
  6. 6.
    Dittmer, D.C. and Christy, M.E., J. Am. Chem. Soc., 1962, vol. 84, p. 399.CrossRefGoogle Scholar
  7. 7.
    Hasek, R.H., Gott, P.G., Meen, R.H., and Martin, G.C., J. Org. Chem., 1963, vol. 28, p. 2496.Google Scholar
  8. 8.
    Dittmer, D.C., Chang, P.L.-F., Davis, F.A., Iwanami, M., Stamos, I.K., and Takahashi, K., J. Org. Chem., 1972, vol. 37, p. 1111.CrossRefGoogle Scholar
  9. 9.
    Woolhouse, A.D., Gainsford, G.J., and Crump, D.R., J. Heterocycl. Chem., 1993, vol. 30, p. 873.Google Scholar
  10. 10.
    Kurosawa, W., Kan, T., and Fukuyama, T., Org. Synth., 2002, vol. 79, p. 186.Google Scholar
  11. 11.
    Fukuyama, T., Jow, C.-K., and Cheung, M., Tetrahedron Lett., 1995, vol. 36, p. 6373.CrossRefGoogle Scholar
  12. 12.
    Miller, S.C. and Scanlan, T.S., J. Am. Chem. Soc., 1997, vol. 119, p. 2301.CrossRefGoogle Scholar
  13. 13.
    Fukuyama, T., Cheung, M., Jow, C.-K., Hidai, Y., and Kan, T., Tetrahedron Lett., 1997, vol. 38, p. 5831.CrossRefGoogle Scholar
  14. 14.
    Iselin, B., Helv. Chim. Acta, 1961, vol. 44, p. 61.CrossRefGoogle Scholar
  15. 15.
    Khaliullin, F.A., Kataev, V.A., and Strokin, Yu.V., Khim. Geterotsikl. Soedin., 1991, p. 516.Google Scholar
  16. 16.
    Fokin, A.V. and Kolomiets, A.F., Khimiya tiiranov (Chemistry of Thiiranes), Moscow: Nauka, 1978.Google Scholar
  17. 17.
    von Braun, J., Ber., 1904, vol. 37, p. 2809.Google Scholar
  18. 18.
    Reverdin, F., Helv. Chim. Acta, 1929, vol. 12, p. 1053.CrossRefGoogle Scholar
  19. 19.
    Hinsberg, O., Justus Liebigs Ann. Chem., 1895, vol. 265, p. 178.Google Scholar
  20. 20.
    Marvel, C.S., Helfrick, M.D., and Belsley, J.H., J. Am. Chem. Soc., 1929, vol. 51, p. 1273.Google Scholar
  21. 21.
    Lellman, E., Ber., 1883, vol. 16, p. 594.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • V. V. Sokolov
    • 1
  • A. N. Butkevich
    • 1
  • V. N. Yuskovets
    • 1
  • A. A. Tomashevskii
    • 1
  • A. A. Potekhin
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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