Skip to main content
Log in

Synthesis and thermal decomposition of hydrotrioxide obtained by ozonization of exo-bicyclo[2.2.1]heptan-2-ol

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Low-temperature (−70 °C) ozonization of exo-bicyclo[2.2.1]heptan-2-ol in CCl3F led to a hydrotrioxide, which was identified by 1H NMR spectroscopy. Kinetics of decomposition of given hydrotrioxide was studied by analysis of the chemiluminescence fading in the IR range of the spectrum and the activation parameters of the process were calculated. Singlet oxygen (1Δg) served as an emitter of eradiation. Yields of 1O2 in a range of temperature from −31.0 to +12.5 °C were determined (at −31 °C the yield was 37.6%). Bicyclo[2.2.1]heptan-2-one was found to be the main product of decomposition of the hydrotrioxide (the yield was 98%).

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

References

  1. B. Plesniçar, in Organic Polyoxides, Ed. W. Ando, J. Wiley and Sons, Chichester, 1992, 479.

    Google Scholar 

  2. V. V. Shereshovets, S. L. Khursan, V. D. Komissarov, and G. A. Tolstikov, Usp. Khim., 2001, 70, 123 [Russ. Chem. Rev., 2001, 70, 105 (Engl. Transl.)].

    Google Scholar 

  3. W. Adam, D. V. Kazakov, and V. P. Kazakov, Chem. Rev., 2005, 105, 3371.

    Article  CAS  Google Scholar 

  4. B. Plesniçar, F. Kovaç, and M. Schara, J. Am. Chem. Soc., 1988, 110, 214.

    Article  Google Scholar 

  5. N. Ya. Shafikov, R. A. Sadykov, V. V. Shereshovets, A. A. Panasenko, and V. D. Komissarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 1923 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981, 30, 1588 (Engl. Transl.)].

  6. V. V. Shereshovets, F. A. Galieva, and V. D. Komissarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 304 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 230 (Engl. Transl.)].

    Google Scholar 

  7. V. V. Shereshovets, F. A. Galieva, R. A. Sadykov, V. D. Komissarov, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2208 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 2025 (Engl. Transl.)].

  8. Q. J. Niu and G. D. Mendenhall, J. Am. Chem. Soc., 1992, 114, 165.

    Article  CAS  Google Scholar 

  9. S. L. Khursan, A. F. Khalizov, E. V. Avzyanova, M. Z. Yakupov, and V. V. Shereshovets, Zh. Phys. Khim., 2001, 75, 1225 [Russ. J. Phys. Chem., 2001, 75, 1107 (Engl. Transl.)].

    CAS  Google Scholar 

  10. Kh. S. Bagdasar’yan, Usp. Khim., 1984, 53, 1073 [Russ. Chem. Rev., 1984, 53, 623 (Engl. Transl.)].

    CAS  Google Scholar 

  11. V. V. Shereshovets, F. A. Galieva, and V. D. Komissarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 1668 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 33, 1529 (Engl. Transl.)].

    Google Scholar 

  12. R. F. Vasil’ev, Usp. Phys. Nauk, 1966, 89, 409 [Soviet. Phys. Uspekhi, 1967, 9, 504 (Engl. Transl.)].

    CAS  Google Scholar 

  13. V. V. Shereshovets, N. Ya. Shafikov, F. A. Galieva, R. A. Sadykov, R. A. Panasenko, and V. D. Komissarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 1177 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982, 31, 1050 (Engl. Transl.)].

  14. A. F. Khalizov, S. L. Khursan, and V. V. Shereshovets, Izv. Akad. Nauk, Ser. Khim., 2001, 60 [Russ. Chem. Bull., Int. Ed., 2001, 50, 63].

    Google Scholar 

  15. T. Tuttle, J. Cerkovnik, B. Plesniçar, and D. Cremer, J. Am. Chem. Soc., 2004, 126, 16093.

    Google Scholar 

  16. E. V. Avzyanova, Q. K. Timerghazin, A. F. Khalizov, S. L. Khursan, L. V. Spirikhin, and V. V. Shereshovets, J. Phys. Org. Chem., 2000, 13, 87.

    Article  CAS  Google Scholar 

  17. M. Zarth and A. de Meijere, Chem. Ber., 1985, 118, 2429.

    Article  CAS  Google Scholar 

  18. E. Eržen, J. Cerkovnik, and B. Plesniçar, J. Org. Chem., 2003, 68, 9129.

    Article  Google Scholar 

  19. E. P. Busel, T. L. Bushueva, and E. A. Burshteyn, Optiks and Spektroskopy, 1970, 29, 501 [Opt. Spectrosc., 1970, 29 (Engl. Transl.)].

    CAS  Google Scholar 

  20. J. Lee and G. W. Robinson, J. Chem. Phys., 1984, 81, 1203.

    Article  CAS  Google Scholar 

  21. P. Wentworth, Jr, L. H. Jones, A. D. Wentworth, X. Y. Zhy, N. A. Larsen, I. A. Wilson, X. Xu, W. A. Goddard, III, K. D. Janda, A. Eschenmoser, and R. A. Lerner, Science, 2001, 293, 1806.

    Article  CAS  Google Scholar 

  22. P. T. Nyffeler, L. Eltepu, N. A. Boyle, C.-H. Wong, A. Eschenmoser, R. A. Lerner, and P. Wentworth, Jr, Angew. Chem., Int. Ed., 2004, 43, 4656.

    Article  CAS  Google Scholar 

  23. J. Cerkovnik, T. Tuttle, E. Kraka, N. Lendero, B. Plesniçar, and D. Cremer, J. Am. Chem. Soc., 2006, 128, 4090.

    Article  CAS  Google Scholar 

  24. X. Xu, R. P. Muller, and W. A. Goddard, III, Proc. Natl Acad. Sci. USA, 2002, 99, 3376.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. A. Grabovskiy.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 263–266, February, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abdrakhmanova, A.R., Khalitova, L.R., Spirikhin, L.V. et al. Synthesis and thermal decomposition of hydrotrioxide obtained by ozonization of exo-bicyclo[2.2.1]heptan-2-ol. Russ Chem Bull 56, 271–275 (2007). https://doi.org/10.1007/s11172-007-0044-x

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0044-x

Key words

Navigation