Skip to main content
SpringerLink
Log in

Quantum-Chemical Investigation of the Mechanism of Fluorocyclization of Norbornenecarboxylic Acids by the Action of F-TEDA-BF4

  • Published:
Theoretical and Experimental Chemistry Aims and scope

Abstract

Possible paths for the reaction of norbornenecarboxylic acids with model F-TEDA-BF4 were studied by the semiempirical PM3 method. The activation energies of the main transformations in the initial reagents and intermediates were determined. Conclusions were reached about the effect of their reaction mechanisms on the distribution of the products.

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. Yu. I. Gevaza, V. I. Staninets, and N. S. Zefirov, Electrophilic Intramolecular Cyclization of Olefins [in Russian], Naukova Dumka, Kiev (1990).

    Google Scholar 

  2. H. C. Sawaguchi, S. Hara, T. Fukuhara, and N. Yoneda, J. Fluor. Chem., 104, No. 2, 277-280 (2000).

    Google Scholar 

  3. M. Albert, K. Dax, and J. Ortner, Tetrahedron, 54, No. 19, 4839-4848 (1998).

    Google Scholar 

  4. S. P. Vincent, M. D. Burkart, C.-Y. Tsai, et al., J. Org. Chem., 64, No. 14, 5264-5279 (1999).

    Google Scholar 

  5. G. S. Lal, G. P. Pez, and R. G. Syvret, Chem. Rev., 96, No. 5, 1737-1755 (1996).

    Google Scholar 

  6. Yu. A. Serguchev, L. F. Lourie, G. V. Polishchuk, et al., Mendeleev Commun., No. 3, 115-117 (2002).

  7. M. Zupan, Pr. Òkulj, and S. Stavberg, Tetrahedron, 57, No. 50, 10027-10031 (2001).

    Google Scholar 

  8. J. J. P. Stewart, J. Comput.-Aided Mol. Design, 4, No. 1, 1-105 (1990).

    Google Scholar 

  9. A. M. Nesterenko, M. V. Ponomarenko, L. F. Lur'e, et al., 38, No. 3, 153-158 (2002).

  10. G. G. Furin and A. A. Faizil'berg, Usp. Khim., 68, No. 8, 725-759 (1999).

    Google Scholar 

  11. A. Pross, Accounts Chem. Res., 18, No. 3, 212-225 (1985).

    Google Scholar 

  12. K. P. Butin, Zh. Ros. Khim. Obshch. im. D. I. Mendeleeva, 45, No. 2, 11-34 (2001).

    Google Scholar 

  13. J. I. Seeman, Chem. Rev., 83, No. 2, 83-134 (1983).

    Google Scholar 

  14. P. Brunelle, T. S. Sorensen, and C. Taeschler, J. Org. Chem., 67, No. 8, 7294-7302 (2001).

    Google Scholar 

  15. G. S. Hammond, J. Am. Chem. Soc., 77, No. 2, 334-340 (1955).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans'ka Vul., 02094, Kyiv, Ukraine

    A. M. Nesterenko, G. V. Polishchuk, L. F. Lur'e & Yu. A. Serguchev

Authors
  1. A. M. Nesterenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. V. Polishchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. F. Lur'e
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. A. Serguchev
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nesterenko, A.M., Polishchuk, G.V., Lur'e, L.F. et al. Quantum-Chemical Investigation of the Mechanism of Fluorocyclization of Norbornenecarboxylic Acids by the Action of F-TEDA-BF4 . Theoretical and Experimental Chemistry 39, 139–146 (2003). https://doi.org/10.1023/A:1024979206036

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024979206036

Search

Navigation