Relative stability of isomeric carbocations with migrating groups in the neighboring positions

Article

Abstract

The relative stabilities of isomeric 9,9-dimethyl-10-R- and 9-R-9,10-dimethylphenanthrenyl, as well as of 3-R-2,3-diphenylbutan-2-yl and 1-R-2-methyl-1,2-diphenylpropan-1-yl cations, were determined in terms of the density functional theory. The equilibrium isomer ratio was found to depend to an appreciable extent on steric requirements of the substituents.

References

  1. 1.
    Genaev, A.M. and Shubin, V.G., Izv. Ross. Akad. Nauk, Ser. Khim., 2006, p. 1045.Google Scholar
  2. 2.
    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
  3. 3.
    Shubin, V.G., Korchagina, D.V., Derendyaev, B.G., Borodkin, G.I., and Koptyug, V.A., Zh. Org. Khim., 1973, vol. 9, p. 1031.Google Scholar
  4. 4.
    Loktev, V.F., Korchagina, D.V., and Shubin, V.G., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1978, vol. 12, no. 5, p. 135.Google Scholar
  5. 5.
    Loktev, V.F., Korchagina, D.V., Shakirov, M.M., and Shubin, V.G., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1978, vol. 12, no. 5, p. 146.Google Scholar
  6. 6.
    Borodkin, G.I., Shakirov, M.M., Shubin, V.G., and Koptyug, V.A., Zh. Org. Khim., 1978, vol. 14, p. 989.Google Scholar
  7. 7.
    Loktev, V.F., Korchagina, D.V., and Shubin, V.G., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1980, vol. 14, no. 6, p. 86.Google Scholar
  8. 8.
    Chikinev, V.A., Bushmelev, V.A., Shakirov, M.M., and Shubin, V.G., Zh. Org. Khim., 1986, vol. 22, p. 1454.Google Scholar
  9. 9.
    Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2004, vol. 40, p. 966.CrossRefGoogle Scholar
  10. 10.
    Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2006, vol. 42, p. 100.CrossRefGoogle Scholar
  11. 11.
    Artamoshkin, V.G., Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2006, vol. 42, p. 1257.CrossRefGoogle Scholar
  12. 12.
    Genaev, A.M., Sal’nikov, G.E., and Shubin, V.G., Russ. J. Org. Chem., 2010, vol. 46, p. 311.CrossRefGoogle Scholar
  13. 13.
    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
  14. 14.
    Olah, G.A., Porter, R.D., Jeuell, C.L., and White, A.M., J. Am. Chem. Soc., 1972, vol. 94, p. 2044.CrossRefGoogle Scholar
  15. 15.
    Bushmelev, V.A., Genaev, A.M., Sal’nikov, G.E., and Shubin, V.G., Russ. J. Org. Chem., 2010, vol. 46, p. 520.CrossRefGoogle Scholar
  16. 16.
    Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 173.Google Scholar
  17. 17.
    Imre, G., Jákli, I., Kalászi, A., and Farkas, Ö., Abstracts of Papers, 1st European Chemistry Congress, Budapest, Hungary, Aug 27–31, 2006.Google Scholar
  18. 18.
    Rocha, G.B., Freire, R.O., Simas, A.M., and Stewart, J.J.P., J. Comput. Chem., 2006, vol. 27, p. 1101.CrossRefGoogle Scholar
  19. 19.
    Stewart, J.J.P., MOPAC2009, Colorado Springs, CO, USA: Stewart Computational Chemistry, 2008; http://OpenMOPAC.net.Google Scholar
  20. 20.
    Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.CrossRefGoogle Scholar
  21. 21.
    Laikov, D.N., Chem. Phys. Lett., 2005, vol. 416, p. 116.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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