Russian Journal of Organic Chemistry

, Volume 47, Issue 6, pp 862–868 | Cite as

Behavior of 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium: Opening of the cyclopropane ring

Article

Abstract

According to the NMR data, opening of the cyclopropane ring in carbocations derived from 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium follows two pathways, depending on the acidity. The first pathway is protonation of the cyclopropyl group; it occurs in strongly acidic medium (HSO3F-SbF5-SO2ClF-CD2Cl2). The second pathway involves cyclopropyl-carbinyl rearrangement; it is typical of less acidic medium.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    DePuy, C.H., Top. Curr. Chem., 1973, vol. 40, p. 73.Google Scholar
  2. 2.
    East, A.L.L., Bučko, T., and Hafner, J., J. Chem. Phys., 2009, vol. 131, p. 104 314.CrossRefGoogle Scholar
  3. 3.
    Wessjohann, L.A., Brandt, W., and Thiemann, T., Chem. Rev., 2003, vol. 103, p. 1625.CrossRefGoogle Scholar
  4. 4.
    Genaev, A.M., Sal’nikov, G.E., and Shubin, V.G., Russ. J. Org. Chem., 2010, vol. 46, p. 311.CrossRefGoogle Scholar
  5. 5.
    Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2006, vol. 42, p. 100.CrossRefGoogle Scholar
  6. 6.
    Bushmelev, V.A., Genaev, A.M., Osadchii, S.A., Shakirov, M.M., and Shubin, V.G., Russ. J. Org. Chem., 2003, vol. 39, p. 1301.CrossRefGoogle Scholar
  7. 7.
    Artamoshkin, V.G., Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2006, vol. 42, 1257.Google Scholar
  8. 8.
    Pittman, C.U. and Miller, W.G., J. Am. Chem. Soc., 1973, vol. 95, p. 2947.CrossRefGoogle Scholar
  9. 9.
    Bushmelev, V.A. and Koptyug, V.A., Zh. Org. Khim., 1970, vol. 6, p. 1853.Google Scholar
  10. 10.
    Rặzuş, A.C., Bartha, E., Arvay, Zs., Osadchii, S.A., Mamatyuk, V.I., and Shubin, V.G., Rev. Roum. Chim., 1991, vol. 36, p. 1307.Google Scholar
  11. 11.
    Shubin, V.G., Korchagina, D.V., Derendyaev, B.G., Mamatyuk, V.I., and Koptyug, V.A., Zh. Org. Khim., 1970, vol. 6, p. 2066.Google Scholar
  12. 12.
    Sorensen, T.S. and Rajeswari, K., J. Am. Chem. Soc., 1971, vol. 93, p. 4222.CrossRefGoogle Scholar
  13. 13.
    Branan, B.M. and Paquette, L.A., J. Am. Chem. Soc., 1994, vol. 116, p. 7658.CrossRefGoogle Scholar
  14. 14.
    Woyski, M.M., J. Am. Chem. Soc., 1950, vol. 72, p. 919.CrossRefGoogle Scholar
  15. 15.
    Imre, G., Jákli, I., Kalászi, A., and Farkas, Ö., Advanced Automatic Generation of 3D Molecular Structures. 1st European Chemistry Congress, Budapest, Hungary, August 27–31, 2006.Google Scholar
  16. 16.
    Chang, C. and Gilson, M.K., J. Comput. Chem., 2003, vol. 24, p. 1987.CrossRefGoogle Scholar
  17. 17.
    Rocha, G.B., Freire, R.O., Simas, A.M., and Stewart, J.J.P., J. Comput. Chem., 2006, vol. 27, p. 1101.CrossRefGoogle Scholar
  18. 18.
    Stewart, J.J.P., MOPAC2009, Colorado Springs, CO, USA: Stewart Computational Chemistry, 2008; http://OpenMOPAC.net.Google Scholar
  19. 19.
    Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.CrossRefGoogle Scholar
  20. 20.
    Laikov, D.N., Chem. Phys. Lett., 2005, vol. 416, p. 116.CrossRefGoogle Scholar
  21. 21.
    Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151; Laikov, D.N. and Ustynyuk, Yu.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, p. 804.CrossRefGoogle Scholar
  22. 22.
    Bain, A.D. and Duns, G.J., Can. J. Chem., 1996, vol. 74, p. 819.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • A. M. Genaev
    • 1
  • G. E. Sal’nikov
    • 1
  • V. G. Shubin
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

Personalised recommendations