Advertisement

Russian Journal of Organic Chemistry

, Volume 48, Issue 10, pp 1302–1308 | Cite as

Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide

  • Kh. M. Alimardanov
  • O. A. SadygovEmail author
  • N. I. Garibov
  • M. Ya. Abdullaeva
Article

Abstract

Optimal conditions were found for induced hydroxyhalogenation of cyclic dienes (tetrahydroindene, 4-vinylcyclohexene and 5-vinyl- and 5-cyclohexenylbicyclo[2.2.1]hept-2-enes) in the system [MHlg-HA or HHlg]-H2O2 (or NaClO). Dehydrohalogenation of the chloro- and bromohydrins thus obtained with powdered potassium carbonate gave the corresponding diepoxy derivatives, and their hydrolysis led to mixtures of stereoisomeric tetrahydric alcohols.

Keywords

Diene Oxirane Metal Halide Chlorohydrin Hydrohalic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Paquin, A.M., Epoxydverbindungen und Epoxydharze, Berlin: Springer, 1958.CrossRefGoogle Scholar
  2. 2.
    Korshak, V.V., Termostoikie polimery (Heat-Resistant Polymers), Moscow: Nauka, 1969.Google Scholar
  3. 3.
    Kameyama, A., Watanabe, Sh., Kobayashi, E., and Nishikubo, T., Macromolecules, 1992, vol. 25, no. 9, p. 2307.CrossRefGoogle Scholar
  4. 4.
    Wu, S., Jorgensen, J.D., and Soucek, M.D., Polymer, 2000, vol. 41, p. 81.CrossRefGoogle Scholar
  5. 5.
    Wang, Z., Xie, M., Zhoo, Y., Yu, Y., and Fang, S., Polymer, 2003, vol. 44, p. 923.CrossRefGoogle Scholar
  6. 6.
    Kheifits, L.A. and Dashunin, V.M., Dushistye veshchestva i drugie produkty dlya parfyumerii (Fragrance Substances and Other Materials for Perfumery), Moscow: Khimiya, 1994.Google Scholar
  7. 7.
    Mashkovskii, K.L., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2002, 15th ed., vols. 1, 2.Google Scholar
  8. 8.
    Livshchits, R.M. and Vobrvinskii L.A., Zameniteli rastitel’nykh masel v lakokrasochnoi promyshlennosti (Vegetable Oil Substitutes in Paint-and-Lacquer Industry), Moscow: Khimiya, 1987.Google Scholar
  9. 9.
    Prilezhaeva, E.N., Reaktsiya Prilezhaeva. Elektrofil’noe okislenie (Prilezhaev Reaction. Electrophilic Oxidation), Moscow: Nauka, 1974; Kas’yan, L.I., Seferova, M.F., and Okovityi, S.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxy Compounds. Methods of Synthesis), Dnepropetrovsk: Dnepropetr. Gos. Univ., 1996.Google Scholar
  10. 10.
    Guiard, S., Giorgi, M., Santelli, M., and Parrain, J.-L., J. Org. Chem., 2003, vol. 68, p. 3319.CrossRefGoogle Scholar
  11. 11.
    Tolstikov, G.A., Reaktsiya gidroperoksidnogo okisleniya (Hydroperoxide Oxidation), Moscow: Nauka, 1976.Google Scholar
  12. 12.
    Nozhnin, I.A., Mel’nik, L.V., Egorova, L.M., and Kryukov, S.I., Neftekhimiya, 1997, vol. 37, no. 2, p. 160.Google Scholar
  13. 13.
    Leonov, V.N., Katalizatory epoksidirovaniya olefinov organicheskimi gidroperoksidami (Catalysts for Olefin Epoxidation with Organic Hydroperoxides), Moscow: TsNIIENeftekhim, 1993.Google Scholar
  14. 14.
    Landau, R., Brown, D., Russel, J.L., and Collar, R., Book of Synopses, 7th World Petroleum Congress, Mexico, 1967.Google Scholar
  15. 15.
    Sheng, M.N. and Zajacek, J.G., J. Org. Chem., 1970, vol. 35, p. 1839.CrossRefGoogle Scholar
  16. 16.
    Lazurin, E.A., Voronenkov, V.V., and Osokin, Yu.G., Usp. Khim., 1997, vol. 46, p. 1739.Google Scholar
  17. 17.
    Antonova, T.N., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2008, vol. 51, no. 4, p. 38.Google Scholar
  18. 18.
    Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Alicyclic Epoxy Compounds. Reactivity), Dnepropetrovsk: Dnepropetr. Gos. Univ., 2003.Google Scholar
  19. 19.
    Alimardanov, Kh.M., Sadygov, O.A., Gadzhiev, T.A., Abdullaeva, M.Ya., Asirova, R.B., and Babaev, N.R., Prots. Neftekhim. Nefteper., 2007, no. 5, p. 66.Google Scholar
  20. 20.
    Muganlinskii, F.F., Treger, Yu.A., and Lyushin, M.M., Khimiya i tekhnologiya galogenorganicheskikh soedinenii (Chemistry and Technology of Organohalogen Compounds), Moscow: Khimiya, 1991.Google Scholar
  21. 21.
    Sadygov, O.A. and Alimardanov, Kh.M., Russ. J. Org. Chem., 2007, vol. 43, p. 1661.CrossRefGoogle Scholar
  22. 22.
    Veliev, M.G., Sadygov, O.A., Alimardanov, Kh.M., and Shatirova, M.I., Russ. J. Org. Chem., 2007, vol. 43, p. 1604.CrossRefGoogle Scholar
  23. 23.
    Sadygov, O.A. and Alimardanov, Kh.M., Russ. J. Org. Chem., 2009, vol. 45, p. 166.CrossRefGoogle Scholar
  24. 24.
    Sadygov, O.A., Alimardanov, Kh.M., and Abbasov, M.F., Russ. J. Gen. Chem., 2009, vol. 79, p. 1698.CrossRefGoogle Scholar
  25. 25.
    Veliev, M.G., Sadygov, O.A., Shatirova, M.I., and Alimardanov, Kh.M., Russ. J. Org. Chem., 2008, vol. 44, p. 1282.CrossRefGoogle Scholar
  26. 26.
    Plate. A.F. and Belikova, N.A., Zh. Obshch. Khim., 1960, vol. 30, p. 3945.Google Scholar
  27. 27.
    Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958.Google Scholar
  28. 28.
    Ionin, B.I. and Ershov, B.A., YaMR spektry v organicheskoi khimii (NMR Spectra in Organic Chemistry), Leningrad: Khimiya, 1967.Google Scholar
  29. 29.
    Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • Kh. M. Alimardanov
    • 1
  • O. A. Sadygov
    • 1
    Email author
  • N. I. Garibov
    • 1
  • M. Ya. Abdullaeva
    • 1
  1. 1.Mamedaliev Institute of Petrochemical ProcessesNational Academy of Sciences of AzerbaijanBakuAzerbaijan

Personalised recommendations