Skip to main content
Log in

Synthesis of thiols from isobornylphenols

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

Abstract

4-(3-Sulfanylpropyl)-2-isobornyl-6-methylphenol and 4-(sulfanylmethyl)-2,6-diisobornylphenol were synthesized from the corresponding 4-(bromoalkyl)phenols according to known procedures. Isobornylphenol with a trimethylene linker was converted into thiol by alkaline hydrolysis of thiouronium salt. The methylene-bridged analog was obtained by reduction of S-benzyl thioacetate with LiAlH4.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Pinko, P.I., Terakh, E.I., Gorokh, E.A., Nikulina, V.V., Prosenko, A.E., and Grigor’ev, I.A., Russ. J. Appl. Chem., 2002, vol. 75, p. 1660.

    Article  CAS  Google Scholar 

  2. Barrett, G.C., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 3.

  3. Kemelev, E.A., Vasyunina, E.A., Sinitsina, O.I., Khomchenko, A.S., Gross, M.A., Kandalintseva, N.V., Prosenko, A.E., and Nevinskii, G.A., Russ. J. Bioorg. Chem., 2008, vol. 34, p. 499.

    Article  Google Scholar 

  4. Zenkov, N.K., Men’shchikova, E.B., Kandalintseva, N.V., Oleinik, A.S., Prosenko, A.E., Gusachenko, O.N., Shklyaeva, O.A., Vavilin, V.A., and Lyakhovich, V.V., Biochemistry (Moscow), 2007, vol. 72, p. 644.

    Article  CAS  Google Scholar 

  5. Kandalintseva, N.V., Trubnikova, Yu.N., and Prosenko, A.E., Chem. Sustainable Dev., 2011, vol. 19, no. 6, p. 545.

    Google Scholar 

  6. Chukicheva, I.Yu., Buravlev, E.V., Fedorova, I.V., Borisenkov, M.F., and Kutchin, A.V., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, p. 2276.

    Article  CAS  Google Scholar 

  7. Pinko, P.I., Cand. Sci. (Chem.) Dissertation, Novosibirsk, 2003.

  8. Han, C.-C. and Balakumar, R., Tetrahedron Lett., 2006, vol. 47, p. 8255.

    Article  CAS  Google Scholar 

  9. Chukicheva, I.Yu., Sukrusheva, O.V., Shumova, O.A., Mazaletskaya, L.I., Shevchenko, O.G., and Kuchin, A.V., Russ. J. Gen. Chem., 2016, vol. 86, p. 2052.

    Article  CAS  Google Scholar 

  10. Buravlev, E.V., Chukicheva, I.Yu., Shevchenko, O.G., Suponitsky, K.Yu., and Kutchin, A.V., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 1232.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. V. Sukrusheva.

Additional information

Original Russian Text © I.Yu. Chukicheva, O.V. Sukrusheva, A.V. Kutchin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 514–518.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chukicheva, I.Y., Sukrusheva, O.V. & Kutchin, A.V. Synthesis of thiols from isobornylphenols. Russ J Org Chem 53, 520–524 (2017). https://doi.org/10.1134/S1070428017040042

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017040042

Navigation