Skip to main content
SpringerLink
Log in

Substitution reaction with participation of organoaluminum compounds. Communication 5. Skeletal rearrangements in reactions of trialkylalanes with tosylates of certain homoallylic alcohols of the terpene series

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The reactions of nopyl tosylates and 4α-hydroxymethyl-Δ2-carene with Et3Al and (i-Bu)3Al are accompanied by skeletal rearrangements, leading to bi- and tricyclic hydrocarbons, containing small rings. The previously unknown rearrangement of nopyl tosylate into brendane series of hydrocarbons has been established.

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

Literature cited

  1. G. A. Tolstikov, A. Yu. Spivak, S. I. Lomakina, and A. V. Kuchin, Izv. Akad. Nauk SSSR, Ser. Khim., 1109 (1985).

  2. F. Negishi, Organometallics in Organic Synthesis, Vol. 1, Wiley, New York (1980), p. 105–127.

    Google Scholar 

  3. M. Nanack and H.-I. Schneider, Angew. Chem. Int. Ed., Engl.,4, 976 (1965).

    Google Scholar 

  4. Yu. G. Bundel' (editor), Carbonium Ions [in Russian], Mir, Moscow (1976), pp. 371–426.

    Google Scholar 

  5. A. Nickon, H. R. Kwasnik, C. T. Mathew, T. D. Swartz, and R. O. Williams, and J. B. DiGiorgio, J. Org. Chem.,43, 3904 (1978).

    Google Scholar 

  6. W. Adam, N. Carballeira, E.-M. Peters, K. Peters, and H. G. von Schnering, J. Am. Chem. Soc.,105, 5132 (1983).

    Google Scholar 

  7. I. I. Bardyshev, A. I. Sedel'nikov, and T. S. Tikhonova, Izd. Akad. Nauk Bel. SSR, 66 (1975).

  8. W. Cocker and H. Lauder, J. Chem. Soc. Perkin Trans. I, 332 (1975).

    Google Scholar 

  9. P. de Mayo, Terpenoids [Russian translation], Inostr. Lit (1963), p. 90.

  10. W. Oocker, P. V. R. Shannon, and P. A. Staniland, J. Chem. Soc. C, 41 (1966).

    Google Scholar 

  11. J. Graefe, L. W. Thanh, and M. Mühlstadt, Z. Chem.,11, 304 (1971).

    Google Scholar 

  12. V. I. Lysenkov, T. I. Pekhk, E. T. Lippmaa, and T. L. Zheleznyak, Zh. Org. Khim.,17, 1616 (1981).

    Google Scholar 

  13. G. Casanova and V. Waegell, J. Org. Chem.,44, 3976 (1979).

    Google Scholar 

  14. G. Levy and G. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley (1972).

  15. P. J. Kropp, D. C. Heckert, and T. J. Flautt, Tetrahedron,24, 1385 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa

    G. A. Tolstikov, A. Yu. Spivak, L. M. Khalilov, E. V. Vasil'eva, S. I. Lomakina & I. A. Ivanova

Authors
  1. G. A. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Spivak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. V. Vasil'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. I. Lomakina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. A. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 4, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1814–1820, August, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tolstikov, G.A., Spivak, A.Y., Khalilov, L.M. et al. Substitution reaction with participation of organoaluminum compounds. Communication 5. Skeletal rearrangements in reactions of trialkylalanes with tosylates of certain homoallylic alcohols of the terpene series. Russ Chem Bull 34, 1662–1667 (1985). https://doi.org/10.1007/BF00948514

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00948514

Keywords

Search

Navigation