Skip to main content
SpringerLink
Log in

Addition of perfluoroalkanoic acids to (R)-(+)-limonene

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

Abstract

Perfluoroalkanoic acids with different lengths of the perfluoroalkyl radical selectively add under mild conditions to the exocyclic double C=C of limonene to give the corresponding Markovnikov adducts, α-terpinyl perfluoroalkanoates. The reaction in the presence of sulfuric acid 0°C involves both double C=C bonds in the limonene molecule with formation of p-menthane-1,8-diyl bis(perfluoroalkanoates).

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. Rice, P.J. and Coats, J.R., Pestic. Sci., 1994, vol. 41, p. 195.

    Article  CAS  Google Scholar 

  2. Roberts, R.M.G., J. Chem. Soc., Perkin Trans. 2, 1976, p. 1374.

    Google Scholar 

  3. De Mattos, M.C.S., Coelho, R.B., and Sanseverino, A.M., Synth. Commun., 2004, vol. 34, p. 541.

    Article  Google Scholar 

  4. Yuasa, Y. and Yuasa, Y., Org. Process Res. Dev., 2006, vol. 10, p. 1231.

    Article  CAS  Google Scholar 

  5. Breitmaier, E., Jung, G., Voelter, W., and Bayer, E., Tetrahedron, 1970, vol. 26, p. 2053.

    Article  CAS  Google Scholar 

  6. Erman, W.F., Chemistry of the Monoterpenes: An Encyclopedic Handbook, New York: Marcel Dekker, 1985, part A.

    Google Scholar 

  7. Erman, W.F., Chemistry of the Monoterpenes: An Encyclopedic Handbook, New York: Marcel Dekker, 1985, part B.

    Google Scholar 

  8. Tietze, L.-F. and Eicher, T., Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Stuttgart: Georg Thieme, 1991, 2nd ed.

    Book  Google Scholar 

  9. Surburg, H. and Panten, J., Common Fragrance and Flavor Materials. Preparation, Properties and Uses, Weinheim: Wiley-VCH, 2006, 5th ed., p. 56.

    Book  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological University of Plant Polymers, ul. Ivana Chernykh 4, St. Petersburg, 198095, Russia

    Yu. G. Trishin, M. V. Shafeeva & L. A. Tamm

Authors
  1. Yu. G. Trishin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Shafeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. A. Tamm
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. G. Trishin.

Additional information

Dedicated to the memory of the Master, Corresponding Member of the Russian Academy of Sciences A.A. Petrov, on the 100th anniversary of his birth

Original Russian Text © Yu.G. Trishin, M.V. Shafeeva, L.A. Tamm, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 4, pp. 561–566.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Trishin, Y.G., Shafeeva, M.V. & Tamm, L.A. Addition of perfluoroalkanoic acids to (R)-(+)-limonene. Russ J Org Chem 49, 545–550 (2013). https://doi.org/10.1134/S1070428013040088

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013040088

Keywords

Search

Navigation