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Tetrafluoroboric acid — A new catalyst for the synthesis of 1,3-dioxolanes. Preparation of hydroxyacetone

Abstract

It is established that tetrafluoroboric acid (HBF4) is an effective catalyst for halogen substitution reactions of oxiranes (epichlorohydrin and 1-bromo-3-methyl-2,3-epoxybutane) with aldehydes and ketones, forming 1,3-dioxolanes in high yields.

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Literature Cited

  1. 1.

    M. S. Malinovskii,Oxides of Olefins and Their Derivatives [in Russian], Goskhimizdat, Moscow (1961).

  2. 2.

    G. Buz and D. Martin,Chemistry of Boron Trifluoride and Its Derivatives [Russian translation], IL, Moscow (1955).

  3. 3.

    A. S. Mueller, US Patent, No. 33,055,665;Chem. Abstr.,66, 86249 (1967).

  4. 4.

    G. Maerker, E. I. Haeberer, and W. C. Ault,J. Am. Oil Chemists' Soc.,41, 584 (1964);Chem. Abstr.,61, 11887 (1964).

  5. 5.

    A. A. Petrov,Zh. S. Khim., No. 11, 981 (1940).

  6. 6.

    W. R. Hardie and J. E. Aaron, US Patent, No. 3,629,287;Refer. Zh. Khim., No. 20, N 288 (1972).

  7. 7.

    P. I. Kazaryan, S. V. Avakyan, and A. A. Gevorkyan,Arm. Khim. Zh.,35, No. 12, 801 (1982).

  8. 8.

    G. S. Alieva, L. G. Truzhenikova, and I. N. Belova,Zh. Obshch. Khim.,32, 3634 (1962).

  9. 9.

    J. Gelas,Bull. Soc. Chim. Fr., No. 6, 2341 (1970).

  10. 10.

    P. I. Kazaryan, S. V. Avakyan, A. A. Gevorkyan, O. G. Kulinkovich, and G. A. Panosyan,Khim. Geterotsikl. Soedin., No. 12, 1607 (1983).

  11. 11.

    N. V. Kuznetsov and R. A. Myrsina,Ukr. Khim. Zh.,36, No. 10, 1050 (1970).

  12. 12.

    Veigand-Khil'getag,Experimental Techniques in Organic Chemistry [in Russian], Khimiya, Moscow (1968), p. 272.

  13. 13.

    Syntheses of Organic Preparations, Collection 2 [Russian translation], IL, Moscow (1949), pp. 74–75.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 33–36, January, 1991.

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Gevorkyan, A.A., Kazaryan, P.I., Avakyan, O.V. et al. Tetrafluoroboric acid — A new catalyst for the synthesis of 1,3-dioxolanes. Preparation of hydroxyacetone. Chem Heterocycl Compd 27, 27–30 (1991). https://doi.org/10.1007/BF00633210

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Keywords

  • Organic Chemistry
  • Aldehyde
  • Ketone
  • Halogen
  • Substitution Reaction