Skip to main content
Log in

Features of the synthesis of unsaturated sulfides proceeding from (2-chloroprop-2-en-1-yl)isothiouronium chloride

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Procedure of synthesis of sulfides containing a chloropropenyl fragment sensitive to bases was modified. The change in the sequence of reagents addition ensuring a contact of isothiouronium salt with a minimal base quantity and the application of a mixture hydrazine hydrate-alkali allowed the preparation of target sulfides under mild conditions in up to 93% yields.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Koval’, I.V., Russ. Chem. Rev., 1994, vol. 63, p. 323.

    Article  Google Scholar 

  2. Koval’, I.V., Russ. Chem. Rev., 1994, vol. 63, p. 147.

    Article  Google Scholar 

  3. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 3. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1983, vol. 5.

    Google Scholar 

  4. Levanova, E.P., Grabel’nykh, V.A., Elaev, A.V., Russavkaya, N.V., Klyba, L.V., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2013, vol. 83, p. 1341.

    Article  CAS  Google Scholar 

  5. Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S., Russavkaya, N.V., Albanov, A.I., Klyba, L.V., Tarasova, O.A., Rozentsveig, I.B., and Korchevin, N.A., Russ. J. Gen. Chem., 2013, vol. 83, p. 1660.

    Article  CAS  Google Scholar 

  6. Becker, H.G.O., Domschke, G., Fanghänel, E., Fischer, M., Gewald, K., Mayer, R., Pavel, D., Schmidt, H., Schwetlick, K., Berger, W., Faust, J., Gentz, F., Gluch, R., Müller, K., Schollberg, K., Seiler, E., and Zeppenfeld, G., Organikum, Veb Deutsher Verlag der Wissenschaften, Berlin, 1990. Translated under the title Organikum, Moscow: Khimiya, 1992, vol. 1.

    Google Scholar 

  7. Luzzio, F.A. and Little, A.D., Synth. Commun., 1984, vol. 14, p. 209.

    Article  CAS  Google Scholar 

  8. Hengchang, C., Zhengzhou, L., and Wei, L., Synth. Commun., 1990, vol. 20, p. 3313.

    Article  Google Scholar 

  9. Levanova, E.P., Grabelnykh, V.A., Vahrina, V.S., Albanov, A.I., Klyba, L.V., Russavskaya, N.V., Korchevin, N.A., and Rozentsveig, I.B., J. Sulfur Chem., 2014, vol. 35, p. 179.

    Article  CAS  Google Scholar 

  10. Bottini, A.T. and Böttner, E.F., J. Org. Chem., 1966, vol. 31, p. 385.

    Article  CAS  Google Scholar 

  11. Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V., Klyba, L.V., Zhanchipova, E.R., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2009, vol. 79, p. 1097.

    Article  CAS  Google Scholar 

  12. Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S., Russavskaya, N.V., Albanov, A.I., Rozentsveig, I.B., and Kochevin, N.A., Russ. J. Gen. Chem., 2014, vol. 84, p. 439.

    Article  CAS  Google Scholar 

  13. Deryagina, E.N., Russavskaya, N.V., Papernaya, L.K., Levanova, E.P., Sukhomazova, E.N., and Korchevin, N.A., Russ. Chem. Bull., 2005, vol. 54, p. 2473.

    Article  CAS  Google Scholar 

  14. Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S., Russavskaya, N.V., Albanov, A.I., Korchevin, N.A., and Rozentsveig, I.B., Russ. J. Org. Chem., 2014, vol. 50, p. 429.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. P. Levanova.

Additional information

Original Russian Text © E.P. Levanova, V.S. Vakhrina, V.A. Grabel’nykh, I.B. Rozentsveig, N.V. Russavskaya, A.I. Albanov, E. R. Sanzheeva, N.A. Korchevin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 175–180.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Levanova, E.P., Vakhrina, V.S., Grabel’nykh, V.A. et al. Features of the synthesis of unsaturated sulfides proceeding from (2-chloroprop-2-en-1-yl)isothiouronium chloride. Russ J Org Chem 51, 161–166 (2015). https://doi.org/10.1134/S1070428015020037

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015020037

Keywords

Navigation