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Oxidation of alkenes with hydrogen peroxide, catalyzed by boron trifluoride. Synthesis of vicinal methoxyalkanols

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Abstract

In oxidation of alkenes with the BF3-H2O2 system, boron trifluoride induces transfer of available oxygen from hydrogen peroxide, accompanied by the formation of epoxides. The oxidation in methanol occurs as a one-pot two-step process involving epoxidation of the C=C bond followed by opening of the oxirane ring, with the formation of methoxyalkanols.

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References

  1. Tojo, G. and Fernandez, M., Oxidation of Alcohols to Aldehydes and Ketones: a Guide to Current Common Practice, New York: Springer, 2006.

    Google Scholar 

  2. Meyer, F. and Limberg, C., Organometallic Oxidation Catalysis, Top. Organomet. Chem., 2007, vol. 22.

  3. Tolstikov, G.A., Reaktsii gidroperekisnogo okisleniya (Reactions of Hydroperoxide Oxidation), Moscow: Nauka, 1976.

    Google Scholar 

  4. Jones, C.W., Applications of Hydrogen Peroxide and Derivatives, Royal Soc. Chem., 1999.

  5. Strukul, G., Catalytic Oxidations with Hydrogen Peroxide as Oxidant, Springer, 1992.

  6. Lane, B.S. and Burgess, K., Chem. Rev., 2003, vol. 103, no. 7, p. 2457.

    Article  CAS  Google Scholar 

  7. Butler, A., Clague, M.J., and Meister, G.E., Chem. Rev., 1994, vol. 94, no. 3, p. 625.

    Article  CAS  Google Scholar 

  8. McKillop, A. and Sanderson, W.R., J. Chem. Soc., Perkin Trans. 1, 2000, no. 4, p. 471.

  9. Terent’ev, A.O., Kutkin, A.V., Platonov, M.M., Vorontsov, I.I., Antipin, M.Yu., Ogibin, Yu.N., and Nikishin, G.I., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, no. 3, p. 650.

  10. Davies, A.G., Foster, R.V., and White, A.M., J. Chem. Soc., 1954, p. 2200.

  11. Milas, N.A. and Perry, L.H., J. Am. Chem. Soc., 1946, vol. 68, no. 10, p. 1938.

    Article  CAS  Google Scholar 

  12. Carlqvis, P., Eclend, R., and Brinck, T., J. Org. Chem., 2001, vol. 66, no. 4, p. 1193.

    Article  Google Scholar 

  13. McClure, J.D. and Williams, P.H., J. Org. Chem., 1962, vol. 27, no. 1, p. 24.

    Article  CAS  Google Scholar 

  14. Petrov, A.A., Zh. Obshch. Khim., 1940, vol. 10, no. 11, p. 981.

    CAS  Google Scholar 

  15. Liu, Y.-J., Chu, T.-Y., and Engel, R., Synth. Commun., 1992, vol. 22, no. 16, p. 2367.

    Article  CAS  Google Scholar 

  16. Guivisdalsky, P.N. and Bittman, R., J. Am. Chem. Soc., 1989, vol. 111, no. 8, p. 3077.

    Article  CAS  Google Scholar 

  17. Guivisdalsky, P.N. and Bittman, R., J. Org. Chem., 1989, vol. 54, no. 19, p. 4637.

    Article  CAS  Google Scholar 

  18. Guivisdalsky, P.N. and Bittman, R., J. Org. Chem., 1989, vol. 54, no. 19, p. 4643.

    Article  CAS  Google Scholar 

  19. Kas’yan, L.I., Stepanova, N.V., Belyakova, T.A., Kunanets, V.K., Lutsenko, A.I., and Zefirov, N.S., Zh. Org. Khim., 1984, vol. 20, no. 11, p. 2295.

    CAS  Google Scholar 

  20. Kas’yan, L.I., Stepanova, N.V., Galafeeva, M.F., Boldeskul, I.E., Trachevskii, V.V., and Zefirov, N.S., Zh. Org. Khim., 1987, vol. 23, no. 1, p. 122.

    CAS  Google Scholar 

  21. Iranpoor, N. and Baltork, I.M., Synth. Commun., 1990, vol. 20, no. 18, p. 2789.

    Article  CAS  Google Scholar 

  22. Hatsui, T. and Takeshita, H., Bull. Chem. Soc. Jpn., 1980, vol. 53, no. 9, p. 2655.

    Article  CAS  Google Scholar 

  23. Saito, I., Nagata, R., Yuba, K., and Matsuura, T., Tetrahedron Lett., 1983, vol. 24, no. 16, p. 1737.

    Article  CAS  Google Scholar 

  24. Antonovskii, V.L. and Buzlanova, M.M., Analiticheskaya khimiya organicheskikh peroksidov (Analytical Chemistry of Organic Peroxide), Moscow: Khimiya, 1978.

    Google Scholar 

  25. Barluenga, J., Vazquez-Villa, H., Ballesteros, A., and Gonzalez, J.M., Org. Lett., 2002, vol. 17, no. 4, p. 2817.

    Article  Google Scholar 

  26. Nicolaou, K.C., Montagnon, T., Ulven, T., Baran, P.S., Zhong, Y.-L., and Sarabia, F., J. Am. Chem. Soc., 2002, vol. 124, no. 20, p. 5718.

    Article  CAS  Google Scholar 

  27. Lane, B.S., Vogt, M., DeRose, V.J., and Burgess, K., J. Am. Chem. Soc., 2002, vol. 124, no. 40, p. 11946.

  28. Geng, X.-L., Wang, Z., Li, X.-Q., and Zhang, C., J. Org. Chem., 2005, vol. 70, no. 23, p. 9610.

    Article  CAS  Google Scholar 

  29. Betzemeier, B., Lhermitte, F., and Knochel, P., Synth. Lett., 1999, no. 4, p. 489.

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Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    A. O. Terent’ev, K. A. Boyarinova & G. I. Nikishin

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  1. A. O. Terent’ev
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  2. K. A. Boyarinova
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  3. G. I. Nikishin
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Correspondence to A. O. Terent’ev.

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Original Russian Text © A.O. Terent’ev, K.A. Boyarinova, G.I. Nikishin, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 4, pp. 611–615.

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Terent’ev, A.O., Boyarinova, K.A. & Nikishin, G.I. Oxidation of alkenes with hydrogen peroxide, catalyzed by boron trifluoride. Synthesis of vicinal methoxyalkanols. Russ J Gen Chem 78, 592–596 (2008). https://doi.org/10.1134/S1070363208040130

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  • DOI: https://doi.org/10.1134/S1070363208040130

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