Skip to main content
Log in

Synthesis and investigation of certain properties of C-functional derivatives of (3)-1,2-dicarbaundecaborate

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

Conclusions

  1. 1.

    A series of C-functional derivatives of (3)-1,2-dicarbaundecaborate was synthesized and some of their properties were studied.

  2. 2.

    Apparent ionization constants of acids of the (3)-1,2-dicarbaundecaborate series were measured and it was found that they are very weak carboxylic acids.

  3. 3.

    Upon reaction with excess LiA1H4, under mild conditions the carbonyl,\(\begin{array}{*{20}c} \backslash \\ {CH(OH)} \\ / \\ \end{array}\), and CH2OH groups of dicarbaundecaborate ketones and alcohols are reduced to CH2 and CH3 groups, respectively.

  4. 4.

    The effect of Grignard reagent on ketones and esters of the dicarbaundecarbprate series was studied and it was established that the composition of reaction products depends both on the steric hindrance of the carbonyl group and on the electron-donating effect of the (3)-1,2-dicarbaundecaborate substituent.

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

Literature cited

  1. L. I. Zakharkin and V. S. Kozlova, Zh. Obshch. Khim.,43, 1097 (1973); Izv. Akad. Nauk SSSR, Ser. Khim., 1135 (1973).

    Google Scholar 

  2. L. I. Zakharkin, V. S. Kozlova, and S. A. Babich, Zh. Obshch. Khim.,44, 1891 (1974).

    Google Scholar 

  3. L. I. Zakharkin and V. N. Kalinin, Dokl. Akad. Nauk SSSR,163, 110 (1965).

    Google Scholar 

  4. A. I. L'vov, Dissertation [in Russian], Moscow (1967).

  5. L. I. Zakharkin, Yu. A. Chapovskii, V. A. Brattsev, and V. I. Stanko, Zh. Obshch. Khim.,36, 878 (1966).

    Google Scholar 

  6. V. I. Stanko, A. I. Klitnova, Yu. A. Chapovskii, and T. P. Klimova, Zh. Obshch. Khim.,38, 1779 (1966).

    Google Scholar 

  7. A. N. Snyakin, Dissertation [in Russian], Moscow (1971).

  8. R. A. Alger and M. F. Hawthorne, J. Amer. Chem. Soc.,92, 6174 (1970).

    Google Scholar 

  9. É. G. Perevalova, K. N. Grandberg, N. I. Zharikova, S. P. Gubin, and A. N. Nesmeyanov, Izv. Akad. Nauk SSSR, Ser. Khim., 832 (1966).

  10. L. A. Cohen and W. H. Jones, J. Amer. Chem. Soc.,85, 3397 (1963).

    Google Scholar 

  11. R. A. Wiesboek and M. F. Hawthorne, J. Amer. Chem. Soc.,86, 1642 (1964).

    Google Scholar 

  12. M. Charton, J. Org. Chem.,29, 1222 (1964).

    Google Scholar 

  13. B. R. Brown and A. B. S. White, J. Chem. Soc., 3155 (1957).

  14. A. Gaset and A. Lattes, J. Organometal. Chem.,71, 1 (1974).

    Google Scholar 

  15. L. I. Zakharkin and A. V. Kazantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 568 (1966).

  16. M. E. Hawthorne, C. Y. Donald, and P. M. Garret, J. Amer. Chem. Soc.,90, 862 (1968).

    Google Scholar 

  17. A. Albert and E. Sargent, Determination of Ionization Constants, Halsted Press (1971).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1107–1113, May, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zakharkin, L.I., Kirillova, V.S. Synthesis and investigation of certain properties of C-functional derivatives of (3)-1,2-dicarbaundecaborate. Russ Chem Bull 25, 1076–1082 (1976). https://doi.org/10.1007/BF00921996

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00921996

Keywords

Navigation