Chemistry of Natural Compounds

, Volume 44, Issue 6, pp 724–727 | Cite as

Oxidation of secondary terpene alcohols by chlorine dioxide

  • L. L. FrolovaEmail author
  • A. V. Popov
  • S. A. Rubtsova
  • A. V. Kuchin

Secondary terpene alcohols cis- and trans-verbenol, neo-iso-verbanol, borneol, iso-borneol, and menthol were oxidized by chlorine dioxide into the corresponding ketones. It was shown that the nature of the solvent and catalyst and the structure of the starting compound, including the stereochemistry of the hydroxyl, influenced the oxidation process.

Key words

cis- and trans-verbenol neo-iso-verbanol borneol iso-borneol menthol chlorine dioxide oxidation catalysts 



The work was supported by the RF President (Program of Support for Leading Scientific Schools, Grant NSh-4028.2008.3) and the Russian Foundation for Basic Research (Grant No. 05-03-33005).


  1. 1.
    B. G. Gordon, R. G. Kieffer, and D. H. Rosenblatt, J. Prog. Inorg. Chem., 15, 201 (1972).CrossRefGoogle Scholar
  2. 2.
    O. M. Lezina, S. A. Rubtsova, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 1779 (2003) [Engl. transl., Russ. Chem. Bull., 8, 1877 (2003)].Google Scholar
  3. 3.
    A. V. Kuchin, S. A. Rubtsova, and I. V. Loginova, Izv. Akad. Nauk, Ser. Khim., 3, 813 (2001) [Engl. transl., Russ. Chem. Bull., 3, 432 (2001)].Google Scholar
  4. 4.
    A. V. Kuchin and L. L. Frolova, Izv. Akad. Nauk, Ser. Khim., 1658 (2000) [Engl. transl., Russ. Chem. Bull., 49, 1647 (2000)].Google Scholar
  5. 5.
    A. V. Kuchin, I. A. Dvornikova, and I. Yu. Nalimova, Izv. Akad. Nauk, Ser. Khim., 2025 (1999) [Engl. transl., Russ. Chem. Bull., 48, 2001 (1999)].Google Scholar
  6. 6.
    A. V. Kuchin, S. A. Rubtsova, and L. P. Karmanova, Izv. Akad. Nauk, Ser. Khim., 2110 (1998) [Engl. transl., Russ. Chem. Bull., 47, 2051 (1998)].Google Scholar
  7. 7.
    RF Pat. No. 2,260,580; Byull. Izobret., 26 (2005).Google Scholar
  8. 8.
    E. S. Suvorkina, Candidate Dissertation in Chemical Sciences, Ufa State Petroleum Technical University, Ufa (2002).Google Scholar
  9. 9.
    H. C. Brown and C. P. Jang, J. Am. Chem. Soc., 83, 2952 (1961).CrossRefGoogle Scholar
  10. 10.
    C. B. Sharma, Rev. Roum. Chim., 28, 11–12, 967 (1983).Google Scholar
  11. 11.
    T. Hirao, Chem. Rev., 97, 8, 2707 (1997).PubMedCrossRefGoogle Scholar
  12. 12.
    G. A. Tolstikov, Hydroperoxide Oxidation Reactions [in Russian], Nauka, Moscow (1976).Google Scholar
  13. 13.
    T. A. Tumanova and I. E. Flis, Physico-Chemical Principles of Cellulose Bleaching [in Russian], Lesnaya Promyshlennost´, Moscow (1972), p. 236.Google Scholar
  14. 14.
    L. L. Frolova, I. V. Dreval´, M. V. Panteleeva, E. U. Ipatova, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 475 (2003) [Engl. transl., Russ. Chem. Bull., 52, 498 (2003)].Google Scholar
  15. 15.
    R. Mori, Agric. Biol. Chem., 40, 415 (1976).Google Scholar
  16. 16.
    RF Pat. No. 2,250,208; Byull. Izobret., 11 (2005).Google Scholar
  17. 17.
    H. M. Colquhoun, New Pathways for Organic Synthesis: Practical Applications of Transition Metals, Plenum Press, New York (1984).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • L. L. Frolova
    • 1
    Email author
  • A. V. Popov
    • 1
  • S. A. Rubtsova
    • 1
  • A. V. Kuchin
    • 1
  1. 1.Institute of Chemistry, Komi Scientific Center, Ural BranchRussian Academy of Sciences, Russian Federationul. PervomaiskayaRussia

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