Russian Journal of Organic Chemistry

, Volume 49, Issue 9, pp 1300–1306 | Cite as

o-Bornylphenol: Stereochemistry and synthesis of new derivatives from its (+)-enantiomer

  • E. V. Buravlev
  • I. Yu. Chukicheva
  • O. A. Shumova
  • K. Yu. Suponitskii
  • A. V. Kutchin


New derivatives of the (+)-enantiomer of o-bornylphenol were synthesized with a view to determine the configuration of chiral centers therein. The absolute configuration of the terpene substituents in the Mannich reaction product obtained from 4,13-diaza-18-crown-6 was estimated as (1R,2R,4S) on the basis of anomalous X-ray scattering.


Chiral Center Bromocresol Purple Isobornyl Final Divergence Factor Light Yellow Oily Substance 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Buravlev, E.V., Chukicheva, I.Y., Suponitsky, K.Y., Vikharev, Y.B., Grishko, V.V., and Kutchin, A.V., Lett. Org. Chem. 2011, vol. 8, p. 301.CrossRefGoogle Scholar
  2. 2.
    Buravlev, E.V., Chukicheva, I.Yu., Shevchenko, O.G., Suponitsky, K.Yu., and Kutchin, A.V., Russ. J. Bioorg. Chem., 2011, vol. 37, p. 614.CrossRefGoogle Scholar
  3. 3.
    Chukicheva, I.Yu., Shumova, O.A., and Kutchin, A.V., Chem. Nat. Compd., 2012, vol. 48, p. 43.CrossRefGoogle Scholar
  4. 4.
    Erman, W.F., J. Am. Chem. Soc., 1964, vol. 86, p. 2887.CrossRefGoogle Scholar
  5. 5.
    Chukicheva, I.Yu., Fedorova, I.V., Buravlev, E.V., Suponitskii, K.Yu., and Kutchin, A.V., Russ. J. Gen. Chem., 2012, vol. 82, p. 1425.CrossRefGoogle Scholar
  6. 6.
    Berkessel, A., Vennemann, M.R., and Lex, J., Eur. J. Org. Chem., 2002, p. 2800.Google Scholar
  7. 7.
    Buravlev, E.V., Chukicheva, I.Yu., Suponitskii, K.Yu., and Kuchin, A.V., Russ. J. Gen. Chem., 2008, vol. 78, p. 1411.CrossRefGoogle Scholar
  8. 8.
    Ma, S.-L., Wang, X.-Z., Fan, C.-H., Guo, Q.-L., Zhu, W.-X., and Zhang, J., J. Mol. Struct., 2007, vol. 846, p. 23.CrossRefGoogle Scholar
  9. 9.
    Chi, K.-W., Wei, H.-C., Kottke, T., and Lagow, R.J., J. Org. Chem., 1996, vol. 61, p. 5684.CrossRefGoogle Scholar
  10. 10.
    Ho, M.-L., Chen, K.-Y., Wu, L.-C., Shen, J.-Y., Lee, G.-H., Ko, M.-J., Wang, C.-C., Lee, J.-F., and Chou, P.-T., Chem. Commun., 2008, p. 2438.Google Scholar
  11. 11.
    Bordunov, A.V., Bradshaw, J.S., Zhang, X.X., Dalley, N.K., Kou, X., and Izatt, R.M., Inorg. Chem., 1996, vol. 35, p. 7229.CrossRefGoogle Scholar
  12. 12.
    Bordunov, A.V., Bradshaw, J.S., Pastushok, V.N., Zhang, X.X., Kou, X., Dalley, N.K., Yang, Z., Savage, P.B., and Izatt, R.M., Tetrahedron, 1997, vol. 53, p. 17 595.CrossRefGoogle Scholar
  13. 13.
    Graf, E., Hosseini, M.W., De Cian, A., and Fischer, J., Tetrahedron Lett., 1998, vol. 39, p. 3501.CrossRefGoogle Scholar
  14. 14.
    Meadows, E.S., De Wall, S.L., Barbour, L.J., Fronczek, F.R., Kim, M.-S., and Gokel, G.W., J. Am. Chem. Soc., 2000, vol. 122, p. 3325.CrossRefGoogle Scholar
  15. 15.
    Bordunov, A.V., Lukyanenko, N.G., Pastushok, V.N., Krakowiak, K.E., Bradshaw, J.S., Dalley, N.K., and Kou, X., J. Org. Chem., 1995, vol. 60, p. 4912.CrossRefGoogle Scholar
  16. 16.
    Buravlev, E.V., Chukicheva, I.Yu., Suponitskii, K.Yu., and Kutchin, A.V., Russ. J. Gen. Chem., 2012, vol. 82, p. 1421.CrossRefGoogle Scholar
  17. 17.
    Towson, J.C., Weismiller, M.C., Sankar Lal, G., Sheppard, A.C., Kumar, A., and Davis, F.A., Organic Syntheses, Freeman, J.P., Ed., New York: Wiley, 1993, collect. vol. 8, p. 104.Google Scholar
  18. 18.
    APEX2 and SAINT Software Package, Madison, Wisconsin, USA: Bruker AXS, 2005.Google Scholar
  19. 19.
    Sheldrick, G.M., Acta. Crystallogr., Sect. A, 2008, vol. 64, p. 112.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • E. V. Buravlev
    • 1
  • I. Yu. Chukicheva
    • 1
  • O. A. Shumova
    • 1
  • K. Yu. Suponitskii
    • 2
  • A. V. Kutchin
    • 1
  1. 1.Institute of Chemistry, Komi Research Center, Ural BranchRussian Academy of SciencesSyktyvkarRussia
  2. 2.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

Personalised recommendations