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Cubane derivatives

5. Synthesis of 1-bromo-9,9-ethylenedioxypentacyclo[4.3.0.02,5.03,8.04,7]non-4-ylcarbinol

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The reduction of 1-bromo-9,9-ethylenedioxypentacyclo[4.3.0.02,5.03,8.04,7]nonane-4-carboxylic acid (2) with lithium aluminum hydride and aluminum hydride in THF was studied. A new effective method for preparing 1-bromo-9,9-ethylenedioxypentacyclo[4.3.0.02,5.03,8.04,7]-non-4-ylcarbinol (1) based on reduction of2 with AlH3 under mild conditions was developed.

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References

  1. V. V., G. P. Bugaeva, M. E. Ivanova, L. B. Romanova, L. T. Eremenko, S. E. Nefedov, and I. L. Eremenko,Izv. Akad. Nauk, Ser. Khim., 1998, 1387 [Russ. Chem. Bull., 1998,47, 1349 (Engl. Transl.)].

  2. A. Coyle,Chemistry in Britain, 1995,31, 183.

    Google Scholar 

  3. T. Carrell, E. A. Winter, A. Bashir-Hashemi, and J. Rebek, Jr.,Angew. Chem. Intern. Edn., 1994,33, 2059.

    Article  Google Scholar 

  4. J. T. Edward, P. G. Farrell, and G. E. Langford,J. Am. Chem. Soc., 1976,98, 3075.

    Article  CAS  Google Scholar 

  5. H. C. Brown, P. M. Weissman, and N. M. Yoon,J. Am. Chem. Soc., 1966,88, 1458.

    Article  CAS  Google Scholar 

  6. S. Krishnamurthy and H. C. Brown,J. Org. Chem., 1980,45, 849.

    Article  CAS  Google Scholar 

  7. H. C. Brown and N. M. Yoon,J. Am. Chem. Soc., 1966,88, 1464.

    Article  CAS  Google Scholar 

  8. A. J. H. Klunder and B. Zwanenburg,Tetrahedron, 1973,29, 161.

    Article  CAS  Google Scholar 

  9. A. J. H. Klunder, and B. Zwanenburg,Tetrahedron, 1973,29, 1683.

    Article  CAS  Google Scholar 

  10. A. J. H. Klunder and B. Zwanenburg,Tetrahedron, 1972,28, 4131.

    Article  CAS  Google Scholar 

  11. L. T. Eremenko, L. B. Romanova, M. E. Ivanova, I. L. Eremenko, S. E. Nefedov, and Yu. T. Struchkov,Izv. Akad. Nauk, Ser. Khim., 1994, 668 [Russ. Chem. Bull., 1994,43, 619 (Engl. Trans.)].

    Google Scholar 

  12. N. M. Yoon and H. C. Brown,J. Am. Chem. Soc., 1968,90, 2927.

    Article  CAS  Google Scholar 

  13. D. L. Schmidt, C. B. Roberts, and T. F. Reigler,Inorg. Synth., 1973,14, 47.

    CAS  Google Scholar 

  14. N. E. Matzek and D. F. Musinski, US Pat. 3818819,Chem. Abstrs. 1974,81, 123768.

  15. N. B. Chapman, J. M. Rey, and K. J. Toyne,J. Org. Chem., 1970,35, 3860.

    Article  CAS  Google Scholar 

  16. D. F. Shriver,The Manipulation of Air-Sensitive Compounds, McGraw-Hill Book Company, New York, 1969, 299.

    Google Scholar 

  17. J. M. Key, Ph.D. Thesis, University of Hull, England, 1968.

Download references

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For Part 4, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2296–2299, November, 1998.

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Zakharov, V.V., Bugaeva, G.P., Andreeva, N.Y. et al. Cubane derivatives. Russ Chem Bull 47, 2226–2228 (1998). https://doi.org/10.1007/BF02494286

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  • DOI: https://doi.org/10.1007/BF02494286

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