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Fluorinated cyclohexadienones as versatile synthons for preparation of organofluorine compounds

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Abstract

The review summarizes the new investigation of the reactivity of polyfluorinated cyclohexadienones: nucleophilic, cycloaddition, and photochemical reactions and, furthermore, such transformations of products of these reactions as reduction, hydrolysis, and photochemical reaction. The use of polyfluorinated cyclohexadienones as highly reactive synthons opens the possibility for the synthesis of a broad variety of otherwise inaccessible fluorinated organic compounds containing functional groups, such as fluorinated derivatives of polyphenyl ethers, arylacetic acids, cyclohexenecarboxylic acids, naphthalene and anthraquinone derivatives bearing the carboxylic group, and some fluorinated heterocyclic compounds.

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References

  1. Chemistry of Organic Fluorine Compounds II. A Critical Review, Eds. M. Hudlicky and A. E. Pavlath, ACS Monograph 187, Washington, DC, 1995, 1296 pp.

  2. L. S. Kobrina and V. D. Shteingarts, J. Fluor. Chem., 1988, 41, 111.

    Google Scholar 

  3. N. E. Akhmetova, A. A. Shtark, and V. D. Shteingarts, Zh. Org. Khim., 1973, 9, 1218 [J. Org. Chem. USSR, 1973, 9 (Engl. Transl.)].

    Google Scholar 

  4. L. S. Kobrina, V. N. Kovtonyuk, and G. G. Yakobson, Zh. Org. Khim., 1977, 13, 1447 [J. Org. Chem. USSR, 1977, 13 (Engl. Transl.)]; V. N. Kovtonyuk, L. S. Kobrina, and G. G. Yakobson, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1984, 2, 119 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1984, 2 (Engl. Transl.)]; V. N. Kovtonyuk, L. S. Kobrina, and G. G. Yakobson, J. Fluor. Chem., 1981, 18, 587; V. N. Kovtonyuk, L. S. Kobrina, and G. G. Yakobson, J. Fluor. Chem., 1985, 28, 89; L. S. Kobrina, N. V. Popkova, and G. G. Yakobson, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 3 No. 7, 125 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 3, No. 7 (Engl. Transl.)]; L. S. Kobrina, N. V. Popkova, and G. G. Yakobson, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 5, No. 12, 140 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 5, No. 12 (Engl. Transl.)]; N. V. Popkova, L. S. Kobrina, and G. G. Yakobson, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 5, No. 12, 110 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, 5, No. 12 (Engl. Transl.)].

    Google Scholar 

  5. V. N. Kovtonyuk and L. S. Kobrina, J. Fluor. Chem., 1993, 63, 243.

    Google Scholar 

  6. B. Miller, J. Org. Chem., 1963, 28, 345.

    Google Scholar 

  7. US Pat. 3525756; Chem. Abstrs., 1970, 73, 98477.

  8. W. Sheppard and C. Sharts, Organic Fluorine Chemistry, Benjamin W. A., Inc., New York, 1969, 602 pp.

    Google Scholar 

  9. K. Somekawa, T. Matsuo, and S. Kumamoto, Bull. Chem. Soc. Jpn., 1969, 42, 3499.

    Google Scholar 

  10. N. E. Akhmetova, N. G. Kostina, V. I. Mamatyuk, A. A. Shtark, and V. D. Shteingarts, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1973, 6, No. 14, 86 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1973, 6, No. 14 (Engl. Transl.)]; N. E. Akhmetova, N. G. Kostina, and V. D. Shteingarts, Zh. Org. Khim., 1979, 15, 2135 [J. Org. Chem. USSR, 1979, 15 (Engl. Transl.)].

    Google Scholar 

  11. V. N. Kovtonyuk, L. S. Kobrina, and G. G. Yakobson, Zh. Org. Khim., 1988, 24, 1952 [J. Org. Chem. USSR, 1988, 24 (Engl. Transl.)].

    Google Scholar 

  12. V. N. Kovtonyuk and L. S. Kobrina, Zh. Org. Khim., 2002, 38, 196 [Russ. J. Org. Chem., 2001, 38 (Engl. Transl.)].

    Google Scholar 

  13. N. E. Akhmetova and V. D. Shteingarts, Zh. Org. Khim., 1977, 13, 1277 [J. Org. Chem. USSR, 1977, 13 (Engl. Transl.)].

    Google Scholar 

  14. V. N. Kovtonyuk and L. S. Kobrina, Zh. Org. Khim., 1991, 27, 2289 [J. Org. Chem. USSR, 1991, 27 (Engl. Transl.)].

    Google Scholar 

  15. V. N. Kovtonyuk and L. S. Kobrina, Zh. Org. Khim., 1999, 35, 82 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].

    Google Scholar 

  16. W. J. Mijs, O. E. Van Lohuizen, J. Bussink, and L. Vollbracht, Tetrahedron, 1967, 23, 2253.

    Google Scholar 

  17. D. J. Williams and R. Kreilick, J. Am. Chem. Soc., 1968, 90, 2775.

    Google Scholar 

  18. V. N. Kovtonyuk, L. S. Kobrina, and G. G. Yakobson, Zh. Org. Khim., 1979, 15, 1447 [J. Org. Chem. USSR, 1979, 15 (Engl. Transl.)].

    Google Scholar 

  19. J. Grobe, D. Le Van, H. Wiese, B. Krebs, M. Läge, and L. S. Kobrina, Z. Naturforsch., Teil B, 1995, 50, 691.

    Google Scholar 

  20. R. F. Stockel, F. Megson, and M. T. Beachem, J. Org. Chem., 1968, 33, 4395; M. A. Howells, R. D. Howells, N. C. Baenziger, and D. J. Burton, J. Am. Chem. Soc., 1973, 95, 5366; D. J. Burton, S. Shinya, and R. D. Howells, J. Am. Chem. Soc., 1979, 101, 3689.

    Google Scholar 

  21. A. J. Waring, in Advances in Alicyclic Chemistry, Eds. H. Hart and G. J. Karabatsos, Acad. Press, New York, 1966, 1, 129.

    Google Scholar 

  22. E. C. Taylor, G. E. Jagdmann, and A. McKillop, J. Org. Chem., 1978, 43, 4385.

    Google Scholar 

  23. K. Auwers and K. Ziegler, Liebigs Ann. Chem., 1921, 425, 280.

    Google Scholar 

  24. E. Bamberger and E. Reber, Ber. Deutsch. Chem. Ges., 1907, 40, 2258; E. Hecker, Chem. Ber., 1959, 92, 3198.

    Google Scholar 

  25. V. N. Kovtonyuk and L. S. Kobrina, Izv. Akad. Nauk, Ser. Khim., 1996, 1778 [Russ. Chem. Bull., 1996, 45, 1688 (Engl. Transl.)].

  26. F. Gozzi and J. S. Siegel, Pure Appl. Chem., 1995, 67, 683.

    Google Scholar 

  27. H. Perst and K. Dimroth, Tetrahedron, 1968, 24, 5385.

    Google Scholar 

  28. H. Greenland, J. T. Pinhey, and S. Sternhell, J. Chem. Soc., Perkin Trans. 1, 1986, 1789; H. Greenland, R. P. Kozyrod, and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1986, 2011.

  29. J. Carnduff, J. Iball, D. G. Leppard, and J. N. Low, J. Chem. Soc., Chem. Commun., 1969, 1218.

  30. V. N. Kovtonyuk and L. S. Kobrina, J. Fluor. Chem., 1994, 66, 219.

    Google Scholar 

  31. F. Wessely, E. Schinzel, G. Spiteller, and P. Klezl, Monatsh. Chem., 1959, 90, 96.

    Google Scholar 

  32. G. Spiteller, G. Schmidt, H. Budzikiewicz, and F. Wessely, Monatsh. Chem., 1960, 91, 129.

    Google Scholar 

  33. F. Wessely, H. Budzikiewicz, and W. Metlesics, Monatsh. Chem., 1959, 90, 121.

    Google Scholar 

  34. F. Wessely, H. Budzikiewicz, and H. Janda, Monatsh. Chem., 1960, 91, 456.

    Google Scholar 

  35. H. Budzikiewicz and J. Gunawan, Monatsh. Chem., 1973, 104, 876; G. Quinkert, G. Dürner, E. Kleiner, F. Adam, E. Haupt, and D. Leibfritz, Chem. Ber., 1980, 113, 2227.

    Google Scholar 

  36. G. Spiteller and F. Wessely, Monatsh. Chem., 1959, 90, 660.

    Google Scholar 

  37. A. G. Schultz and S. Puig, J. Org. Chem., 1985, 50, 915.

    Google Scholar 

  38. A. G. Schultz, K. K. Eng, and R. K. Kullnig, Tetrahedron Lett., 1986, 27, 2331.

    Google Scholar 

  39. V. N. Kovtonyuk, L. S. Kobrina, I. Yu. Bagryanskaya, and Yu. V. Gatilov, Zh. Org. Khim., 1999, 35, 75 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].

    Google Scholar 

  40. V. N. Kovtonyuk, L. S. Kobrina, I. Yu. Bagrjanskaja, Yu. V. Gatilov, R. Frölich, and G. Haufe, J. Chem. Soc., Perkin Trans. 1, 2000, 1929.

  41. M. G. Banwell and M. P. Collis, J. Chem. Soc., Chem. Commun., 1991, 1343

  42. M. R. Bryce, R. D. Chambers, and G. Taylor, J. Chem. Soc., Perkin Trans. 1, 1984, 509.

  43. L. S. Kobrina and V. D. Shteingarts, Zh. Org. Khim., 1988, 24, 1344 [J. Org. Chem. USSR, 1988, 24 (Engl. Transl.)].

    Google Scholar 

  44. L. S. Kobrina and A. A. Bogachev, J. Fluor. Chem., 1993, 62, 243.

    Google Scholar 

  45. A. A. Bogachev, I. Yu. Bagryanskaya, T. V. Rybalova, Yu. V. Gatilov, and L. S. Kobrina, Zh. Obshch. Khim., 1996, 66, 1324 [Russ. J. Gen. Chem., 1996, 66 (Engl. Transl.)].

    Google Scholar 

  46. J. Grobe, D. Le Van, B. Broschk, and L. S. Kobrina, Tetrahedron Lett., 1993, 34, 4619.

    Google Scholar 

  47. M. Regitz, in Multiple Bonds and Low Coordination in Phosphorus Chemistry, Eds. M. Regitz and O. J. Scherer, G. Thieme Verlag, Stuttgart, New York, 1990, 58.

    Google Scholar 

  48. G. Märkl, G. Jin Yu, and E. Silbereisen, Angew. Chem., Int. Ed. Engl., 1982, 21, 370.

    Google Scholar 

  49. U. Annen and M. Regitz, Tetrahedron Lett., 1988, 29, 1681.

    Google Scholar 

  50. U. Annen, M. Regitz, and H. Kluge, Chem. Ber., 1990, 123, 935.

    Google Scholar 

  51. W. Rösch and M. Regitz, Z. Naturforsch., Teil B, 1986, 41b, 931.

    Google Scholar 

  52. M. Regitz, Chem. Rev., 1990, 90, 191.

    Google Scholar 

  53. K. Blatter, W. Rösch, U. J. Vogelbacher, J. Fink, and M. Regitz, Angew. Chem., Int. Ed. Engl., 1987, 26, 85.

    Google Scholar 

  54. A. A. Bogachev, L. S. Kobrina, and V. D. Shteingarts, Izv. Akad. Nauk, Ser. Khim., 1994, 1634 [Russ. Chem. Bull., 1994, 43, 1546 (Engl. Transl.)].

  55. D. Del Mazza and M. C. Reinecke, J. Org. Chem., 1988, 53, 5799; L. Friedman and F. M. Logullo, J. Am. Chem. Soc., 1963, 85, 1549; A. C. G. Gray and H. Hart, J. Am. Chem. Soc., 1968, 90, 2569.

    Google Scholar 

  56. H.-O. Kalinovski, S. Berger, and S. Braun, Carbon-13 NMR Spectroscopy, Wiley, Chichester, 1988, p. 189.

    Google Scholar 

  57. A. A. Bogachev, A. V. Manuilov, and L. S. Kobrina, Zh. Org. Khim., 1996, 32, 1016 [Russ. J. Org. Chem., 1996, 32 (Engl. Transl.)].

    Google Scholar 

  58. A. A. Bogachev, L. S. Kobrina, O. G. L. Meyer, and G. Haufe, J. Fluor. Chem., 1998, 97, 135.

    Google Scholar 

  59. T. Ernet and G. Haufe, Tetrahedron Lett., 1996, 37, 7251.

    Google Scholar 

  60. J. J. P. Stewart, MOPAC93, Fujitsu Limited, Tokyo, 1993.

    Google Scholar 

  61. V. V. Veselovsky, A. S. Gybin, A. V. Lozanova, A. M. Moiseenkov, W. A. Smit, and R. Caple, Tetrahedron Lett., 1988, 29, 175.

    Google Scholar 

  62. A. A. Bogachev and L. S. Kobrina, Zh. Org. Khim., 1997, 33, 1433 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].

    Google Scholar 

  63. A. A. Bogachev and L. S. Kobrina, Zh. Org. Khim., 1997, 33, 742 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].

    Google Scholar 

  64. A. G. Rumyantseva, A. K. Petrov, M. I. Kollegova, and V. A. Barkhash, Zh. Org. Khim., 1972, 8, 1030 [J. Org. Chem. USSR, 1972, 8 (Engl. Transl.)].

    Google Scholar 

  65. R. K. Murray and H. Hart, Tetrahedron Lett., 1968, 4995; J. Ipaktchi, Tetrahedron Lett., 1969, 215.

  66. H. Hart and R. K. Murray, Tetrahedron Lett., 1969, 379.

  67. A. A. Bogachev and L. S. Kobrina, J. Fluor. Chem., 1998, 92, 33.

    Google Scholar 

  68. W. T. Brady, Tetrahedron, 1981, 37, 2949.

    Google Scholar 

  69. N. De Kimpe and R. Verhe, The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, Wiley, Chichester, 1988, 107 pp.

    Google Scholar 

  70. L. P. Anderson, W. J. Feast, and W. K. R. Musgrave, J. Chem. Soc. C, 1969, 211.

  71. K. Alder, F. H. Flock, and H. Lessenich, Chem. Ber., 1957, 90, 1709.

    Google Scholar 

  72. A. C. G. Gray and H. Hart, J. Am. Chem. Soc., 1968, 90, 2569.

    Google Scholar 

  73. A. Oku and H. Hart, J. Org. Chem., 1972, 37, 4969.

    Google Scholar 

  74. A. Oku and A. Matsui, Bull. Chem. Soc. Jpn., 1977, 50, 3338.

    Google Scholar 

  75. I. F. Mikhailova and V. A. Barkhash, Zh. Org. Khim., 1970, 6, 2325 [J. Org. Chem. USSR, 1970, 6 (Engl. Transl.)].

    Google Scholar 

  76. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Eds. R. Filler, Y. Kobayashi, and L. M. Yagupolskii, Elsevier, Amsterdam, 1993, 386 pp.

    Google Scholar 

  77. Biomedical Frontiers of Fluorine Chemistry, Eds. I. Ojima, J. R. McCarthy, and J. T. Welch, ACS Symposium Series 639, Washington, 1996, 356 pp.

  78. M. D. Mashkovskii, Lekarstvennye sredstva [Medicines], Torsing, Kharkov, 1998, 1, 543 pp. (in Russian).

    Google Scholar 

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  1. Siberian Division of the Russian Academy of Sciences, N. N. Vorozhtsov Institute of Organic Chemistry, 9 prosp. Akad. Lavrent"eva, 630090, Novosibirsk, Russian Federation

    L. S. Kobrina

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Kobrina, L.S. Fluorinated cyclohexadienones as versatile synthons for preparation of organofluorine compounds. Russian Chemical Bulletin 51, 1775–1795 (2002). https://doi.org/10.1023/A:1021378713624

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