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Synthesis of peroxides from β,δ-triketones under heterogeneous conditions

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Abstract

Heterogeneous reactions of β,δ-triketones with ethereal hydrogen peroxide in nonpolar solvents, catalyzed by phosphomolybdic acid, afforded mixtures of stereoisomeric ozonides, tricyclic monoperoxides, and bridged tetraoxanes. The trioxolane ring is formed by the carbonyl groups located in the δ-position with respect to each other.

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References

  1. Jones, C.W., Applications of Hydrogen Peroxides and Derivatives, Cambridge, UK: Roy. Soc. Chem., 1999.

    Google Scholar 

  2. Ando, W., Organic Peroxides, Chichester: Wiley, 1992.

    Google Scholar 

  3. Jefford, C.W., Curr. Top. Med. Chem., 2012, vol. 12. p. 373.

    Article  CAS  Google Scholar 

  4. Opsenica, D.M. and Solaja, B.A., J. Serb. Chem. Soc., 2009, vol. 74. p. 1155.

    Article  CAS  Google Scholar 

  5. Yadav, N., Sharma, C., and Awasthi, S.K., RSC Adv., 2014, vol. 4. p. 5469.

    Article  CAS  Google Scholar 

  6. Terent’ev, A.O., Borisov, D.A., and Yaremenko, I.A., Chem. Heterocycl. Compd., 2012, vol. 48. p. 55.

    Article  Google Scholar 

  7. Boissier, J., Portela, J., Pradines, V., Cosledan, F., Robert, A., and Meunier, B., C. R. Chim., 2012, vol. 15. p. 75.

    Article  CAS  Google Scholar 

  8. Keiser, J., Ingram, K., Vargas, M., Chollet, J., Wang, X.F., Dong, Y.X., and Vennerstrom, J.L., Antimicrob. Agents Chemother., 2012, vol. 56. p. 1090.

    Article  CAS  Google Scholar 

  9. Ingram, K., Yaremenko, I.A., Krylov, I.B., Hofer, L., Terent’ev, A.O., and Keiser, J., J. Med. Chem., 2012, vol. 55. p. 8700.

    Article  CAS  Google Scholar 

  10. Rehman, K., Lötsch, F., Kremsner, P.G., and Ramharter, M., Int. J. Infect. Dis., 2014, vol. 29. p. 268.

    Article  CAS  Google Scholar 

  11. Denisov, E.T., Denisova, T.G., and Pokidova, T.S., Handbook of Free Radical Initiators, Hoboken, NJ: Wiley, 2003.

    Book  Google Scholar 

  12. Nesvadba, P., Encyclopedia of Radicals in Chemistry, Biology, and Materials, Chatgilialoglu, C. and Studer, A., Eds., Chichester: Wiley, 2012, vol. 2.

  13. Ray, P., Encyclopedia of Polymer Science and Technology, Hoboken, NJ: Wiley, 2003–2004, 3rd ed.

  14. Engels, H.-W., Weidenhaupt, H.-J., Pieroth, M., Hofmann, W., Menting, K.-H., Mergenhagen, T., Schmoll, R., and Uhrlandt, S., Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2000.

    Google Scholar 

  15. Terent’ev, A.O., Platonov, M.M., Kashin, A.S., and Nikishin, G.I., Tetrahedron, 2008, vol. 64. p. 7944.

    Article  Google Scholar 

  16. Terent’ev, A.O., Platonov, M.M., Sonneveld, E.J., Peschar, R., Chernyshev, V.V., Starikova, Z.A., and Nikishin, G.I., J. Org. Chem., 2007, vol. 72. p. 7237.

    Article  Google Scholar 

  17. Yan, X., Chen, J.L., Zhu, Y.T., and Qiao, C.H., Synlett, 2011, p. 2827.

    Google Scholar 

  18. Hall, J.F.B., Bourne, R.A., Han, X., Earley, J.H., Poliakoff, M., and George, M.W., Green Chem., 2013, vol. 15. p. 177.

    Article  CAS  Google Scholar 

  19. Terent’ev, A.O., Platonov, M.M., Ogibin, Y.N., and Nikishin, G.I., Synth. Commun., 2007, vol. 37. p. 1281.

    Article  Google Scholar 

  20. Azarifar, D., Khosravi, K., and Soleimanei, F., Synthesis, 2009, no. 15. p. 2553.

    Article  Google Scholar 

  21. Pramanik, S. and Ghorai, P., Org. Lett., 2013, vol. 15. p. 3832.

    Article  CAS  Google Scholar 

  22. Terent’ev, A.O., Yaremenko, I.A., Vil’, V.A., Dembitsky, V.M., and Nikishin, G.I., Synthesis, 2013, vol. 45. p. 246.

    Article  Google Scholar 

  23. Terent’ev, A.O., Borisov, D.A., Vil’, V.A., and Dembitsky, V.M., Beilstein J. Org. Chem., 2014, vol. 10. p. 34.

    Article  Google Scholar 

  24. Terent’ev, A.O., Borisov, D.A., Yaremenko, I.A., Chernyshev, V.V., and Nikishin, G.I., J. Org. Chem., 2010, vol. 75. p. 5065.

    Article  Google Scholar 

  25. Terent’ev, A.O., Borisov, D.A., Semenov, V.V., Chernyshev, V.V., Dembitsky, V.M., and Nikishin, G.I., Synthesis, 2011, no. 13. p. 2091.

    Article  Google Scholar 

  26. Yaremenko, I.A., Terent’ev, A.O., Vil’, V.A., Novikov, R.A., Chernyshev, V.V., Tafeenko, V.A., Levitsky, D.O., Fleury, F., and Nikishin, G.I., Chem. Eur. J., 2014, vol. 20. p. 1. 160.

    Article  Google Scholar 

  27. Criegee, R. and Lohaus, G., Chem. Ber., 1953, vol. 86. p. 1.

    Article  CAS  Google Scholar 

  28. Griesbaum, K., Miclaus, V., Jung, I.C., and Quinkert, R.O., Eur. J. Org. Chem., 1998, p. 627.

    Google Scholar 

  29. Kashin, A.S. and Ananikov, V.P., Russ. Chem. Bull., Int. Ed., 2011, vol. 60. p. 2602.

    Article  CAS  Google Scholar 

  30. Christoffers, J., J. Chem. Soc., Perkin Trans. 1. 1997, p. 3141.

    Google Scholar 

  31. Bartoli, G., Bosco, M., Bellucci, M.C., Marcantoni, E., Sambri, L., and Torregiani, E., Eur. J. Org. Chem., 1999, p. 617.

    Google Scholar 

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Correspondence to A. O. Terent’ev.

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Original Russian Text © A.O. Terent’ev, I.A. Yaremenko, A.P. Glinushkin, G.I. Nikishin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1716–1722.

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Terent’ev, A.O., Yaremenko, I.A., Glinushkin, A.P. et al. Synthesis of peroxides from β,δ-triketones under heterogeneous conditions. Russ J Org Chem 51, 1681–1687 (2015). https://doi.org/10.1134/S1070428015120027

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  • DOI: https://doi.org/10.1134/S1070428015120027

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