Skip to main content
Log in

Synthesis of peroxide compounds by the BF3-catalyzed reaction of acetals and enol ethers with H2O2

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Aliphatic and alicyclic gem-bis-hydroperoxides and their derivatives, bis(1-hydroperoxycycloalkyl) and bis(1-hydroperoxyalkyl) peroxides, dispiro- and tetraalkyl-1,2,4,5-tetroxanes were synthesized by the reaction of aliphatic and alicyclic acetals and enol ethers with H2O2 in the presence of BF3 in anhydrous Et2O.

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. A. O. Terent'ev, A. V. Kutkin, M. M. Platonov, Yu. N. Ogibin, and G. I. Nikishin, Tetrahedron Lett., 2003, 44, 7359.

    Google Scholar 

  2. J. L. Vennerstrom, H.-N. Fu, W. Y. Ellis, A. L. Ager, J. K. Wood, S. L. Andersen, L. Gerena, and W. K. Milhous, J. Med. Chem., 1992, 35, 3023.

    Google Scholar 

  3. C. W. Jefford, Adv. Drug Res., 1997, 29, 271.

    Google Scholar 

  4. Y. Dong, H. Matile, J. Chollet, R. Kaminsky, J. K. Wood, and J. L. Vennerstrom, J. Med. Chem., 1999, 42, 1477.

    Google Scholar 

  5. H.-S. Kim, Y. Shibata, Y. Wataya, K. Tsuchiya, A. Masuyama, and M. Nojima, J. Med. Chem., 1999, 42, 2604.

    Google Scholar 

  6. H.-S. Kim, K. Tsuchiya, Y. Shibata, Y. Wataya, Y. Ushigoe, A. Masuyama, M. Nojima, and K. McCullough, J. Chem. Soc., Perkin Trans. 1, 1999, 1867.

  7. K. Tsuchiya, Y. Hamada, A. Masuyama, M. Nojima, K. J. McCullough, H.-S. Kim, Y. Shibata, and Y. Wataya, Tetrahedron Lett., 1999, 40, 4077.

    Google Scholar 

  8. H.-S. Kim, Y. Nagai, K. Ono, K. Begum, Y. Wataya, Y. Hamada, K. Tsuchiya, A. Masuyama, M. Nojima, and K. McCullough, J. Med. Chem., 2001, 44, 2357.

    Google Scholar 

  9. Y. Hamada, H. Tokuhara, A. Masuyama, M. Nojima, H.-S. Kim, K. Ono, N. Ogura, and Y. Wataya, J. Med. Chem., 2002, 45, 1374.

    Google Scholar 

  10. T. Ledaal and T. Solbjor, Acta Chem. Scand., 1967, 21, 1658.

    Google Scholar 

  11. H. Kropf, in Methoden der organische Chemie (Houben-Weyl), Ed. H. Kropf, Bd. E13, Part 1, 1988, 548.

  12. C. W. Jefford, Synth. Comm., 1990, 20, 2589.

    Google Scholar 

  13. G. V. Somov, Ph.D. Thesis, D. I. Mendeleev Moscow Institute of Chemical Technology, Moscow, 1962 (in Russian).

  14. L. I. Zakharkin, I. M. Churilova, and U. V. Anikina, Izv. Akad. Nauk SSSR. Ser. Khim., 1990, 1089[Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 976 (Engl. Transl.)].

  15. F. Elsinger, in Org. Synth., Ed. H. Baumgarten, Wiley, New York, 1973, Coll. Vol. 5, 76.

    Google Scholar 

  16. Weygand-Hilgetag, Organisch-chemische experimentier kunst. Herstellung von Acetalen, 3 Aufg., Eds. G. Hilgetag and A. Martini, Ambrosius Barth Verlag, Leipzig, 1964.

    Google Scholar 

  17. Organikum. Organische-chemisches Grundpraktikum, Reactions of Carbonyl Compounds, 18 Aufg., VEB Deutscher Verlag Wissenschaften, Berlin, 1990, Ch. 7.

  18. H. Meerwein, in Methoden der organische Chemie (Houben-Weyl), Ed. E. Muller, Thieme Verlag, Stuttgart, 1965, Bd. VI/3, p. 199.

    Google Scholar 

  19. I. Saito, R. Nagata, K. Yuba, and T. Matsuura, Tetrahedron Lett., 1983, 24, 1737.

    Google Scholar 

  20. Dictionary of Organic Compounds, Ed. 5, Chapman & Hall, New York-London-Toronto, 1982, 1-7; 1983–1988, Supll. 1-6.

  21. V. L. Antonovskii, Zh. Prikl. Khim., 1967, 40, 2555 [J. Appl. Chem. USSR, 1967, 40 (Engl. Transl.)].

    Google Scholar 

  22. V. L. Antonovskii, L. F. Nesterov, Kh. V. Tsubina, and I. M. Al'shits, Uspekhi khimii organicheskikh perekisnykh soedinenii i autookisleniya [Advances in the Chemistry of Organic Per-oxide Compounds and Self-Oxidation] Khimiya, Moscow, 1969, 100 (in Russian).

    Google Scholar 

  23. M. Sheldrick, SHELXTL-97, Program for Solution and Refinement of Crystal Structure, Bruker AXS Inc., Madison (WI-53719, USA), 1997.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Terent"ev, A.O., Kutkin, A.V., Platonov, M.M. et al. Synthesis of peroxide compounds by the BF3-catalyzed reaction of acetals and enol ethers with H2O2 . Russian Chemical Bulletin 53, 681–687 (2004). https://doi.org/10.1023/B:RUCB.0000035657.58776.cc

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUCB.0000035657.58776.cc

Navigation