Skip to main content
Log in

Homophenalenyl cations, new representatives of homoaromatic systems

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

Abstract

3b,4-exo,4a,5-Tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cation and its endo-epimer were proved by NMR method to belong to a new kind of homoaromatic systems: homophenalenyl carbocations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Sal’nikov, G.E. and Genaev, A.M., Abstracts of Papers, Vseross. nauchn. konf. “Sovremennye problemy org. khim.” (All-Russian Sci. Conf. on Modern Problems of Organic Chemistry), 2007, Novosibirsk.

  2. Winstein, S., J. Am. Chem. Soc., 1959, vol. 81, p. 6524; Winstein, S.Q., Rev. Chem. Soc., 1969, vol. 23, p. 141.

    Article  CAS  Google Scholar 

  3. Williams, R.V., Chem. Rev., 2001, vol. 101, p. 1185.

    Article  CAS  Google Scholar 

  4. Cyracski, M.K., Havenith, R.W.A., Dobrowolski, M.A., Gray, B.R., Krygowski, T.M., Fowler, P.W., and Jenneskens, L.W., Chem. Eur. J., 2007, vol. 13, p. 2201.

    Article  Google Scholar 

  5. Rosokha, S.V. and Kochi, J.K., J. Org. Chem., 2006, vol. 71, p. 9357; Hess, B.A. Jr. and Schaad, L.J., Pure Appl. Chem., 1980, vol. 52, p. 1471; Ilič, P. and Trinajstič, N., J. Org. Chem., 1980, vol. 45, p. 1738.

    Article  CAS  Google Scholar 

  6. Haddon, R.C., J. Am. Chem. Soc., 1975, vol. 97, p. 3608.

    Article  CAS  Google Scholar 

  7. Murata, I. and Nakasuji, K., Tetrahedron Lett., 1973, vol. 14, p. 1591.

    Article  Google Scholar 

  8. Osadchii, S.A., Mikushova, N.V., and Shubin, V.G., Zh. Org. Khim., 1999, vol. 35, p. 1813.

    Google Scholar 

  9. Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Zh. Org. Khim., 2006, vol. 42, p. 236.

    Google Scholar 

  10. Rybalova, T.V., Gatilov, Yu.V., Kochubei, N.V., Osadchii, S.A., and Shubin, V.G., Zh. Strukt. Khim., 1997, vol. 38, p. 1140.

    Google Scholar 

  11. Bushmelev, V.A., Genaev, A.M., Sal’nikov, G.E., and Shubin, V.G., Zh. Org. Khim., 2007, vol. 43, p. 1659.

    Google Scholar 

  12. Barkhash, V.A., Neklassicheskie karbokationy (Non-Classical Carbcations), Novosibirsk: Nauka, 1984, p. 230.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Mamatyuk, V.I., Rezvukhin, A.I., Isaev, I.S., Buraev, V.I., and Koptyug, V.A., Zh. Org. Khim., 1974, vol. 10, p. 662.

    CAS  Google Scholar 

  15. Childs, R.F., Acc. Chem. Res., 1984, vol. 17, p. 347.

    Article  CAS  Google Scholar 

  16. Paquette, L.A., Broadhurst, M.J., Warner, P., Olah, G.A., and Liang, G., J. Am. Chem. Soc., 1973, vol. 95, p. 3386.

    Article  CAS  Google Scholar 

  17. Koptyug, V.A., Kuzubova, L.I., Isaev, I.S., and Mamatyuk, V.I., Zh. Org. Khim., 1970, vol. 6, p. 1843; Childs, R.F. and Winstein, S., J. Am. Chem. Soc., 1974, vol. 96, p. 6409.

    CAS  Google Scholar 

  18. Forsyth, D.A., Spear, R.J., and Olah, G.A., J. Am. Chem. Soc., 1976, vol. 98, p. 2512.

    Article  CAS  Google Scholar 

  19. Olah, G.A., Staral, J.S., Spear, R.J., and Liang, G., J. Am. Chem. Soc., 1975, vol. 97, p. 5489.

    Article  CAS  Google Scholar 

  20. Salnikov, G.E., Genaev, A.M., and Mamatyuk, V.I., Mendeleev Commun., 2003, p. 48.

  21. Krivdin, L.B. and Kalabin, G.A., Spin-spinovoe vzaimodeistvie 13 C-13 C i 13 C-1 H v spektrakh YaMR organicheskikh soedinenii (13C-13C and 13C-1H Spin-Spin Interaction in NMR Spectra of Organic Compounds), Koptyug, R.A., Novosibirsk: Izd. Novosibirsk. Inst. Org. Khim., 1989, p. 3.

    Google Scholar 

  22. Jonsall, G. and Ahlberg, P., J. Am. Chem. Soc., 1986, vol. 108, p. 3819.

    Article  Google Scholar 

  23. Chen, Z., Wannere, C.S., Corminboeuf, C., Puchta, R., and Schleyer, P.v.R., Chem. Rev., 2005, vol. 105, p. 3842.

    Article  CAS  Google Scholar 

  24. Olah, G.A., Liang, G., and Westerman, P., J. Am. Chem. Soc., 1973, vol. 95, p. 3698.

    Article  CAS  Google Scholar 

  25. Genaev, A.M., Sal’nikov, G.E., and Shubin, V.G., Abstracts of Papers, Vseross. nauchn. konf. “Sovremennye problemy org. khim.” (All-Russian Sci. Conf. on Modern Problems of Organic Chemistry), 2007, Novosibirsk.

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

    Article  CAS  Google Scholar 

  27. Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151; Laikov, D.N. and Ustynyuk, Yu.A., Izv. Akad. Nauk, Ser. Khim., 2005, p. 804.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. E. Sal’nikov.

Additional information

Original Russian Text © G.E. Sal’nikov, A.M. Genaev, V.I. Mamatyuk, V.G. Shubin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 7, pp. 1011–1016.

For preliminary communication, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sal’nikov, G.E., Genaev, A.M., Mamatyuk, V.I. et al. Homophenalenyl cations, new representatives of homoaromatic systems. Russ J Org Chem 44, 1000–1005 (2008). https://doi.org/10.1134/S1070428008070099

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008070099

Keywords

Navigation