Skip to main content
SpringerLink
Log in

Pendular rearrangement of epimeric 3b,4,4a,5-tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cations

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

Abstract

The kinetics of degenerate pendular rearrangement of 3b,exo-4,4a,5-tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cation and its endo epimer, generated under conditions ensuring their long life, were studied by dynamic NMR spectroscopy. The rearrangement mechanism is discussed with account taken of the results of quantum-chemical calculations and published data for related rearrangements.

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. Osadchii, S.A., Mikushova, N.V., and Shubin, V.G., Russ. J. Org. Chem., 1999, vol. 35, p. 1777.

    CAS  Google Scholar 

  2. Borodkin, G.I. and Shubin, V.G., Chemistry Rev., 1999, vol. 24, no. 2, p. 1; Borodkin, G.I. and Shubin, V.G., Usp. Khim., 1995, vol. 64, p. 672.

  3. Isaev, I.S., Mamatyuk, V.I., Kuzubova, L.I., Gordymova, T.A., and Koptyug, V.A., Zh. Org. Khim., 1970, vol. 6, p. 2482.

    CAS  Google Scholar 

  4. Childs, R.F. and Winstein, S., J. Am. Chem. Soc., 1974, vol. 96, p. 6409.

    Article  CAS  Google Scholar 

  5. Childs, R.F., Tetrahedron, 1982, vol. 38, p. 567.

    Article  CAS  Google Scholar 

  6. Klärner, F.-G., Top. Stereochem., 1984, vol. 15, p. 1.

    Article  Google Scholar 

  7. Woodward, R.B. and Hoffmann, R., The Conservation of Orbital Symmetry, New York: Academic, 1970. Translated under the title Sokhranenie orbital’noi simmetrii, Moscow: Mir, 1971, p. 140.

    Google Scholar 

  8. Olah, G.A., Reddy, V.P., and Prakash, G.K.S., Chem. Rev., 1992, vol. 92, p. 69.

    Article  CAS  Google Scholar 

  9. Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Russ. J. Org. Chem., 2006, vol. 42, p. 220.

    Article  CAS  Google Scholar 

  10. Brouwer, D.M. and Hogeveen, H., Prog. Phys. Org. Chem., 1972, vol. 9, p. 179.

    Article  CAS  Google Scholar 

  11. Bain, A.D. and Duns, G.J., Can. J. Chem., 1996, vol. 74, p. 819.

    Article  CAS  Google Scholar 

  12. Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    V. A. Bushmelev, A. M. Genaev, G. E. Sal’nikov & V. G. Shubin

Authors
  1. V. A. Bushmelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. Genaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. E. Sal’nikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. G. Shubin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Bushmelev.

Additional information

Dedicated to the memory of Full Member of the Academy of Sciences of the USSR N.N. Vorozhtsov on the 100th anniversary of his birth

Original Russian Text © V.A. Bushmelev, A.M. Genaev, G.E. Sal’nikov, V.G. Shubin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1659–1663.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bushmelev, V.A., Genaev, A.M., Sal’nikov, G.E. et al. Pendular rearrangement of epimeric 3b,4,4a,5-tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cations. Russ J Org Chem 43, 1656–1660 (2007). https://doi.org/10.1134/S1070428007110127

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007110127

Keywords

Search

Navigation