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Products of direct hydroalkoxylation of norbornene with alcohols over H-beta zeolite catalyst

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Abstract

The reaction of direct hydroalkoxylation of norbornene in the presence of H-beta zeolite catalyst has been studied. It has been found that the selectivity for exo-alkoxynorbornanes of the reaction of norbornene with monohydric alcohols (saturated, unsaturated, or aromatic) reaches 98% at a conversion of 78–98% of the unsaturated compound. The reaction of norbornene with diols (ethylene glycol and 2-butene-1,4-diol) in the presence of H-beta zeolite affords mono- and diethers, whose yield and ratio can be controlled by varying reaction parameters.

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References

  1. R. McCague, M. G. Rowlands, S. E. Barrie, and J. Houghton, J. Med. Chem. 33, 3050 (1990).

    Article  CAS  Google Scholar 

  2. J. M. Hanifin, S. C. Chan, J. B. Cheng, et al., J. Invest. Dermatol. 107, 51 (1996).

    Article  CAS  Google Scholar 

  3. M. K. Mamedov, I. N. Gadzhieva, and Kh. M. Alimardanov, Russ. J. Org. Chem. 39, 180 (2003).

    Article  CAS  Google Scholar 

  4. M. K. Mamedov and E. T. Suleimanova, Zh. Org. Khim. 29, 1138 (1993).

    CAS  Google Scholar 

  5. A. F. Plate and T. A. Meerovich, Izv. Akad. Nauk SSSR, No. 2, 219 (1947).

    Google Scholar 

  6. H. C. Brown and M.-H. Reie, J. Am. Chem. Soc. 24, 5646 (1969).

    Article  Google Scholar 

  7. S. A. Shackelford, J. Org. Chem. 44, 3485 (1979).

    Article  CAS  Google Scholar 

  8. D. F. Shellhamer, C. M. Curtis, R. H. Dunham, et al., J. Org. Chem. 50, 2751 (1985).

    Article  CAS  Google Scholar 

  9. D. F. Shellhamer, R. D. Chapman, S. A. Shackelford, et al., J. Chem. Soc., Perkin Trans. 2, No. 2, 787 (1997).

    Google Scholar 

  10. M. J.-L. Tschan, C. M. Thomas, H. Strub, and J.-F. Carpentier, Adv. Synth. Catal. 351, 2496 (2009).

    Article  CAS  Google Scholar 

  11. A. G. Gasanov and A. V. Nagiev, Zh. Org. Khim. 30, 707 (1994).

    CAS  Google Scholar 

  12. D. C. Rosenfeld, S. Shekhar, A. Takemiya, et al., Org. Lett. 8, 4179 (2006).

    Article  CAS  Google Scholar 

  13. R. T. Mathers, C. LeBlond, K. Damodaran, et al., Macromolecules 41, 524 (2008).

    Article  CAS  Google Scholar 

  14. J. G. Taylor, N. Whittall, and K. K. (Mimi) Hii, Chem. Commun., Issue 40, 5103 (2005).

    Google Scholar 

  15. M. J.-L. Tschan, C. M. Thomas, H. Strub, and J.-F. Carpentier, Adv. Synth. Catal. 351, 2496 (2009).

    Article  CAS  Google Scholar 

  16. T. Hirai, A. Hamasaki, A. Nakamura, and M. Tokunaga, Org. Lett. 11, 5510 (2009).

    Article  CAS  Google Scholar 

  17. Y. Oe, T. Ohta, and Y. Ito, Synlett, No. 1, 179 (2005).

    Google Scholar 

  18. T. T. Dang, F. Boeck, and L. Hintermann, J. Org. Chem. 76, 9353 (2011).

    Article  CAS  Google Scholar 

  19. K. Hensen, C. Mahaim, and W. F. Hölderich, Stud. Surf. Sci. Catal. 105, 1133 (1997).

    Article  Google Scholar 

  20. S. Radhakrishnan, J. Franken, and J. A. Martens, Green Chem. 14, 1475 (2012).

    Article  CAS  Google Scholar 

  21. G. Z. Raskil’dina, A. M. Suleimanova, A. N. Kazakova, et al., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 56(10), 29 (2013).

    Google Scholar 

  22. G. Z. Raskil’dina, Yu. G. Borisova, E. A. Mustafina, and N. G. Grigor’eva, in Low-Waste, Resource-Saving Chemical Technologies and Environmental Safety: Proceedings of All-Russia Scientific-Practical Conference with International Participation (Fobos, Sterlitamak, 2013), p. 29 [in Russian].

    Google Scholar 

  23. J. K. Whitesell and M. A. Minton, Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy (Chapman and Hall, London, 1988).

    Google Scholar 

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Correspondence to N. G. Grigor’eva.

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Original Russian Text © G.Z. Raskil’dina, A.M. Suleimanova, A.N. Kazakova, N.G. Grigor’eva, B.I. Kutepov, S.S. Zlotskii, 2015, published in Neftekhimiya, 2015, Vol. 55, No. 2, pp. 162–170.

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Raskil’dina, G.Z., Suleimanova, A.M., Kazakova, A.N. et al. Products of direct hydroalkoxylation of norbornene with alcohols over H-beta zeolite catalyst. Pet. Chem. 55, 154–162 (2015). https://doi.org/10.1134/S0965544115020164

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  • DOI: https://doi.org/10.1134/S0965544115020164

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