Skip to main content
SpringerLink
Log in

Bororganic compounds

327. 2-Boraadamantane and several of its derivatives

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

Conclusions

  1. 1.

    The hydroboration of bicyclo[3.3.1]nona-2,6-diene (I) by diborane, diborane in the presence of methyl borate, or tetraethyldiborane results in the formation of polymeric compounds with the general formula (C9H14BR)x, containing bicyclic fragments of three types, their relative amounts being dependent on the nature of the hydroborating agent.

  2. 2.

    Pyrolysis of the hydroboration products of bicyclo[3.3.1]nona-2,6-diene yields derivatives of 2-boraadamantane.

  3. 3.

    The treatment of the hydroboration products with methyl borate results in the formation of di(dimethoxyboryl)bicyclo[3.3.1]nonane, which, in turn, can undergo cyclization to form 2-methoxy-2-boraadamantane upon heating.

  4. 4.

    The exchange reaction of 2-methoxy-2-boraadamantane with diborane has been used to synthesize the dimer of 2-boraadamantane.

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. B. M. Mikhailov and T. K. Baryshnikova, Izv. Akad. SSSR, Ser. Khim., 2399 (1976); B. M. Mikhailov, M. E. Gurskii, and M. G. Gverdtsiteli, Izv. Akad. Nauk SSSR, Ser. Khim., 2403 (1976); B. M. Mikhailov, G. S.-Ter-Sarkisyan, and N. N. Govorov, Izv. Akad. Nauk SSSR, Ser. Khim., 2756 (1976); Yu. N. Bubnov, A. V. Tsyban', and B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 2842 (1976).

  2. B. M. Mikhailov and V. N. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim., 1137 (1974).

  3. B. M. Mikhailov, T. A. Shchegoleva, and E. M. Shashkova, and E. M. Shashkova, Izv. Akad. Nauk SSSR, Ser. Khim., 982 (1975).

  4. H. Stetter and E. Schwartz, Chem. Ber.,101, 2464 (1968).

    Google Scholar 

  5. H. Stetter and K. Heckel, Tetrahedron Lett., 1907 (1972).

  6. N. V. Averina, Dissertation, Moscow (1972).

  7. J. R. Schaefer, J. C. Lark, C. A. Flegal, and L. M. Honig, J. Org. Chem.,32, 1372 (1967).

    Google Scholar 

  8. H. Stetter and P. Tacke, Chem. Ber.,96, 694 (1965).

    Google Scholar 

  9. H. Meerwein and W. Schürrmann, Liebigs Ann. Chem.,398, 196 (1913).

    Google Scholar 

  10. N. V. Averina and N. S. Zefirov, Zh. Org. Khim.,5, 1991 (1969).

    Google Scholar 

  11. J. R. Schaefer and L. M. Honig, J. Org. Chem.,33, 2655 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    B. M. Mikhailov, T. A. Shchegoleva, E. M. Shashkova & V. G. Kiselev

Authors
  1. B. M. Mikhailov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. A. Shchegoleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. M. Shashkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. G. Kiselev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For communications 323–326 see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 894–901, April, 1977.

We thank A. S. Shashkova for her help in recording and interpreting the NMR spectra.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mikhailov, B.M., Shchegoleva, T.A., Shashkova, E.M. et al. Bororganic compounds. Russ Chem Bull 26, 818–824 (1977). https://doi.org/10.1007/BF01108207

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01108207

Keywords

Search

Navigation