Skip to main content
SpringerLink
Log in

Alkylation of 4,5-dihydro-1H-imidazole-2-thiol with iodomethylsilanes and -siloxanes

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

Abstract

The alkylation of 4,5-dihydro-1H-imidazole-2-thiol with 1-iodomethyl(dimethyl)phenylsilane, 1-(iodomethyl)-1,1,3,3,3-pentamethyldisiloxane, and 1,3-bis(iodomethyl)-1,1,3,3-tetramethyldisiloxane involved iodine-catalyzed cleavage of the Si–Csp 2 and Si–O bonds with liberated (in situ) hydrogen iodide to afford 2-({[(4,5-dihydro-1H-imidazolium-2-ylsulfanyl)methyl]-1,1,3,3-tetramethyldisiloxanylmethyl}sulfanyl)-4,5-dihydro-1H-imidazolium di- and tetraiodides. Replacement of iodide ion in the products by triiodide gives new organosilicon ionic liquids with several charged fragments.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Yan, K., Lok, C.-N., Bierlab, K., and Che, C.-M., Chem. Commun., 2010, vol. 46, p. 7691.

    Article  CAS  Google Scholar 

  2. Lin, I.W.-S., Lok, C.-N., Yan, K., and Che, C.-M., Chem. Commun., 2013, vol. 49, p. 3297.

    Article  CAS  Google Scholar 

  3. Kalinina, T.A., Khamidullina, L.A., Shakhmina, Yu.S., Glukhareva, T.V., Kochubei, A.A., Cherepanova, O.E., Fan, Zh.-J., Zhu, Y.-J., and Morzherin, Yu.Yu., Chem. Heterocycl. Compd., 2016, vol. 52, p. 910.

    Article  CAS  Google Scholar 

  4. Armenta, R. and Sarmiento-Sánchez, J.I., Chem. Heterocycl. Compd., 2016, vol. 52, p. 1002.

    Article  CAS  Google Scholar 

  5. Granik, V.G. and Grigor’ev, N.B., Russ. Chem. Bull., Int. Ed., 2002, vol. 51, p. 1973.

    Article  CAS  Google Scholar 

  6. Johnston, G.A., Clin. Exp. Pharmacol. Physiol., 1992, vol. 19, p. 73.

    Article  CAS  Google Scholar 

  7. Safaev, R.D., Voronkov, M.G., Fuks, S.Yu., Lycheva, T.A., Khitrova, I.L., Belitskii, G.A., Pakhomov, V.Yu., Vlasova, N.N., and Pestunovich, A.E., Dokl. Akad. Nauk, 1992, vol. 322, p. 994.

    CAS  Google Scholar 

  8. Bogatskii, A.V., Luk’yanenko, N.G., and Kirichenko, T.I., Chem. Heterocycl. Compd., 1983, vol. 19, no. 6, p. 577.

    Article  Google Scholar 

  9. Barcza, S., US Patent no. 3 637 735, 1972; Chem. Abstr., 1972, vol. 76, no. 85 915 u.

    Google Scholar 

  10. Barcza, S., US Patent no. 3 780 175, 1973; Chem. Abstr., 1974, vol. 80, no. 60 027 a.

    Google Scholar 

  11. Nomoto, Y., Obase, H., Takai, H., Hirata, T., Teranishi, M., Nakamura, J., Ohno, T., and Kubo, K., Chem. Pharm. Bull., 1990, vol. 38, p. 2467.

    Article  CAS  Google Scholar 

  12. Minch, B.A., Hickenboth, C.R., Karabin, R.F., Zawacky, S.R., Hockswender, T.R., and McCollum, G.J., US Patent no. 2009/0286978 A1.

  13. Bilgin, S., Isi, M., Yilgo, E., and Yilgo, I., Polymer, 2013, vol. 54, p. 6665.

    Article  CAS  Google Scholar 

  14. Harris, K.M. and Rajagopalan, M., US Patent no. 2003/0114624 A1.

  15. Cooper, G.D., J. Am. Chem. Soc., 1954, vol. 76, p. 2500.

    Article  CAS  Google Scholar 

  16. Voronkov, M.G., Vlasova, N.N., and Pozhidaev, Y.N., Appl. Organomet. Chem., 2000, vol. 14, p. 287.

    Article  CAS  Google Scholar 

  17. Voronkov, M.G., Vlasova, N.N., and Pozhidaev, Yu.N., Zh. Prikl. Khim., 1996, vol. 69, p. 705.

    CAS  Google Scholar 

  18. Kushakova, P.M., Ramsh, S.M., and Garabadgiu, A.V., Chem. Heterocycl. Compd., 2006, vol. 42, no. 2, p. 221.

    Article  CAS  Google Scholar 

  19. Ul’yankina, I.V., Zavodskaya, A.V., Parfenov, V.E., Gidaspov, A.A., Shiryaev, A.K., Selezneva, E.V., and Bakharev, V.V., Chem. Heterocycl. Compd., 2016, vol. 52, p. 1054.

    Article  Google Scholar 

  20. Sorokin, M.S., Lopyrev, V.A., Chipanina, N.N., Sherstyannikova, L.V., and Voronkov, M.G., Russ. J. Gen. Chem., 2004, vol. 74, p. 551.

    Article  CAS  Google Scholar 

  21. Uhlig, W., J. Organomet. Chem., 1993, vol. 452, p. 29.

    Article  CAS  Google Scholar 

  22. Voronkov, M.G., Mileshkevich, V.P., and Yuzhelevskii, Yu.A., Siloksanovaya svyaz’ (The Siloxane Bond), Voronkov, M.G., Ed., Novosibirsk: Nauka, 1976, p. 89.

  23. Zhilitskaya, L.V., Yarosh, N.O., Shagun, L.G., Dorofeev, I.A., and Larina, L.I., Chem. Heterocycl. Compd., 2015, vol. 51, p. 381.

    Article  CAS  Google Scholar 

  24. Wu, F.-L., Hussein, W.M., Ross, B.P., and Mc-Geary, R.P., Curr. Org. Chem., 2012, vol. 16, p. 1555.

    Article  CAS  Google Scholar 

  25. Al-Mohammed, N.N., Hussen, R.S.D., Alias, Y., and Abdullah, Z., RSC Adv., 2015, vol. 5, p. 2869.

    Article  CAS  Google Scholar 

  26. Myles, L., Gore, R.G., Spulak, M., Gathergood, N., and Connon, S.J., Green Chem., 2010, vol. 12, p. 1157.

    Article  CAS  Google Scholar 

  27. Myles, L., Gore, R.G., Gathergood, N., and Connon, S.J., Green Chem., 2013, vol. 15, p. 2740.

    Article  CAS  Google Scholar 

  28. Niedermeyer, H., Hallett, J.P., Villar-Garcia, I.J., Huntand, P.A., and Welton, T., Chem. Soc. Rev., 2012, vol. 41, p. 7780.

    Article  CAS  Google Scholar 

  29. Sun, N., Rodriguez, H., Rahman, M., and Rogers, R.D., Chem. Commun., 2011, vol. 47, p. 1405.

    Article  CAS  Google Scholar 

  30. Parmentier, D., Metz, S.J., and Kroon, M.C., Green Chem., 2013, vol. 15, p. 205.

    Article  CAS  Google Scholar 

  31. Reiller, P., Mercier-Bion, F., Gimenez, N., Barre, N., and Miserque, F., Radiochim. Acta, 2006, vol. 94, p. 739.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. O. Yarosh, L. V. Zhilitskaya, L. G. Shagun, I. A. Dorofeev & L. I. Larina

Authors
  1. N. O. Yarosh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. V. Zhilitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. G. Shagun
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. A. Dorofeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. I. Larina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. O. Yarosh.

Additional information

Original Russian Text © N.O. Yarosh, L.V. Zhilitskaya, L.G. Shagun, I.A. Dorofeev, L.I. Larina, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 7, pp. 1053–1057.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yarosh, N.O., Zhilitskaya, L.V., Shagun, L.G. et al. Alkylation of 4,5-dihydro-1H-imidazole-2-thiol with iodomethylsilanes and -siloxanes. Russ J Org Chem 53, 1066–1070 (2017). https://doi.org/10.1134/S107042801707017X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801707017X

Search

Navigation