Synthesis of Organofluorine Compounds

  • R. E. Banks
  • J. C. Tatlow
Part of the Topics in Applied Chemistry book series (TAPP)


Fluoroorganic chemistry is virtually a man-made subject. Indeed, perfluorocarbon chemistry—which straddles organic and inorganic chemistry—is sometimes facetiously referred to as unnatural product chemistry. Fluorometabolites do occur in nature, but they are few in number and only monofluorides have been detected so far.1 The best known is the plant metabolite CH2FCO2H (see Chapter 1); the other nine include the related compounds CH2FCOCH3, 2-fluorocitric acid, F(CH2) n CO2H (n = 9, 13, 15), and F(CH2)8CH=CH(CH2)7CO2H. The most intriguing by far is nucleo-cidin (1), an antibiotic fluoro-sugar derivative produced by the microorganisms Streptomyces calvus.


Mechanistic Category Dipolar Aprotic Solvent Fluorine Chemistry Organofluorine Compound Fluorinating Agent 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    S. L. Neidleman and J. Geigert, Biohalogenation: Principles, Basic Roles and Applications, Ellis, Horwood, Chichester (1986)Google Scholar
  2. M. Meyer and D. O’Hagan, Chem. Br. 28, 785 (1992).Google Scholar
  3. 2.
    M. Hudlicky and T. Hudlicky, in: The Chemistry of Functional Groups, Supplement D: The Chemistry of Halides, Pseudohalides and Azides (S. Patai and Z. Rappoport, eds.), Part 2, p. 1021, Wiley, Chichester (1983).Google Scholar
  4. 3.
    L. German and S. Zemskov (eds.), New Fluorinating Agents in Organic Synthesis, Springer-Verlag, Berlin (1989).Google Scholar
  5. 4.
    J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, Wiley, New York (1991).Google Scholar
  6. 5.
    I. L. Knunyants and G. G. Yakobson (eds.), Syntheses of Fluoroorganic Compounds, Springer-Verlag, Berlin (1985).Google Scholar
  7. 6.
    M. Hudlický, Chemistry of Organic Fluorine Compounds: A Laboratory Manual with Comprehensive Literature Coverage, Ellis Horwood, Chichester (1976; second revised edn.; reissued 1984 and 1992).Google Scholar
  8. 7.
    For a recent overview, see R.E. Banks and J.C. Tatlow, in: Fluorine: The First Hundred Years (1886–1986) (R. E. Banks, D. W. A. Sharp, and J. C. Tatlow, eds.), pp. 251-272, Elsevier Sequoia, Lausanne (1986) [reproduced in J. Fluorine Chem. 33 (1986)].Google Scholar
  9. 8.
    R. Stephens and J. C. Tatlow, Quart. Rev. Chem. Soc. 16, 44 (1962)CrossRefGoogle Scholar
  10. R. E. Banks and H. Goldwhite, Handbook of Experimental Pharmacology, Vol. XX: Pharmacology of Fluorides, Part 1 (F. A. Smith, ed.), p. 1, Springer-Verlag, Berlin (1966).CrossRefGoogle Scholar
  11. 9.
    S. T. Purrington, B. S. Kagen, and T. B. Patrick, Chem. Rev. 86, 997 (1986).CrossRefGoogle Scholar
  12. 10.
    M. R. Kilbourn, Fluorine-18 Labeling of Radiopharmaceuticals, National Academy Press, Washington DC (1990) (Nuclear Medicine Series; NAS-NS-3203).Google Scholar
  13. 11.
    R. J. Lagow, in Ref. 7, p. 321.Google Scholar
  14. 12.
    J. L. Adcock, in Ref. 7, p. 327.Google Scholar
  15. 13.
    K. V. Scherer, K. Yamanouchi, and T. Ono, J. Fluorine Chem. 50, 47 (1990)CrossRefGoogle Scholar
  16. A. C. Sievert, W. R. Tong, and M. J. Nappa, J. Fluorine Chem. 53, 397 (1991).CrossRefGoogle Scholar
  17. 14.
    J. M. Tedder, in: Advances in Fluorine Chemistry (M. Stacey, J. C. Tatlow, and A. G. Sharpe, eds.), Vol. 2, p. 104, Butterworths, London (1961).Google Scholar
  18. 15.
    M. Stacey and J. C. Tatlow, in Ref. 14, Vol. 1, p. 166 (1960); Ref. 7, p. 267.Google Scholar
  19. 16.
    T. Abe and S. Nagase, in: Preparation, Properties, and Industrial Applications of Organofluorine Compounds (R. E. Banks, ed.), p. 19, Ellis Horwood, Chichester (1982).Google Scholar
  20. 17.(a)
    G. A. Boswell, W. C. Ripka, R. M. Scribner, and C. W. Tullock, Org. React. 21, 1 (1974)Google Scholar
  21. (b).
    C. M. Sharts and W. A. Sheppard, Org. React. 21, 125, (1974).Google Scholar
  22. 18.
    A. M. Lovelace, D. A. Rausch, and W. Postelnek, Aliphatic Fluorine Compounds, Reinhold, New York (1958)Google Scholar
  23. W. A. Sheppard and C. M. Sharts, Organic Fluorine Chemistry, Benjamin, New York (1969)Google Scholar
  24. R. D. Chambers, Fluorine in Organic Chemistry, Wiley-Interscience, New York (1973).Google Scholar
  25. 19.(a)
    M. R. Gerstenberger and A. Haas, Angew. Chem., Int. Ed. Engl. 20, 647 (1981)CrossRefGoogle Scholar
  26. (b).
    J. A. Wilkinson, Chem. Rev. 92, 505 (1992).CrossRefGoogle Scholar
  27. 20.
    A. K. Barbour, L. J. Belf, and M. W. Buxton, in Ref. 14, Vol. 3, p. 181 (1963).Google Scholar
  28. 21.
    J. S. Filippo and L. J. Romano, J. Org. Chem. 40, 782 (1975).CrossRefGoogle Scholar
  29. 22.
    A. J. Bloodworm, K. J. Bowyer, and J. C. Mitchell, Tetrahedron Lett. 28, 5347 (1987).CrossRefGoogle Scholar
  30. 23.
    G. G. Yakobson, and N. E. Akhmetova, Synthesis 169 (1983).Google Scholar
  31. 24.
    T. Ando, D. G. Cork, M. Fujita, T. Kimura, and T. Tatsuno, Chem. Lett. 1877 (1988).Google Scholar
  32. 25.
    N. Yoneda, T. Fukuhara, K. Yamagishi, and A. Suzuki, Chem. Lett. 1675 (1987).Google Scholar
  33. 26.
    D. P. Cox, J. Terpinski, and W. Lawrynowicz, J. Org. Chem. 49, 3216 (1984).CrossRefGoogle Scholar
  34. 27.
    S. A. Pogany, G. M. Zentner, and C. D. Ringeisen, Synthesis 718 (1987).Google Scholar
  35. 28.
    G. A. Olah, J. G. Shih, and G. K. S. Prakash, in Ref. 7, p. 377.Google Scholar
  36. 29.
    R. A. Du Boisson, “Fluorodehydroxylation”, PCR Report for September 1988 (available PCR Incorporated, PO Box 1466, Gainesville, FL 21602, USA).Google Scholar
  37. 30.
    P. A. Messina, K. C. Mange, and W. J. Middleton, J. Fluorine Chem. 42, 137 (1989)CrossRefGoogle Scholar
  38. K. C. Mange and W. J. Middleton, J. Fluorine Chem. 43, 405 (1989).CrossRefGoogle Scholar
  39. 31.
    C.-L. J. Wang, Org. React. 34, 319 (1987).Google Scholar
  40. 32.
    A. I. Burmakov, B. V. Kunshenko, A. Alekseeva, and L. M. Yagupolskii, in Ref. 3, p. 197.Google Scholar
  41. 33.
    M. Hudlicky, Org. React. 35, 513 (1988).Google Scholar
  42. 34.
    L. N. Markovskii and V. E. Pashinnik, in Ref. 3, p. 254.Google Scholar
  43. 35.
    W. F Edgell and L. Parts, J. Am. Chem. Soc. 77, 4899 (1955).CrossRefGoogle Scholar
  44. 36.
    D. P. Ashton, T. A. Ryan, B. R. Webster, and B. A. Wolfindale, J. Fluorine Chem. 27, 263 (1985).CrossRefGoogle Scholar
  45. 37.
    J. Cuomo and R. A. Olofson, J. Org. Chem. 44, 1016 (1979)CrossRefGoogle Scholar
  46. V. A. Dang, R. A. Olafson, P. R. Wolf, M. D. Piteau, and J.-R G. Senet, J. Org. Chem. 1847 (1990).Google Scholar
  47. 38.
    H. Garcia, M. C. Perrod, L. Gilbert, S. Ratton, and C. Rochin, J. Fluorine Chem. 54, 111 (1991).CrossRefGoogle Scholar
  48. 39.
    M. Muehlbacher and C. D. Poulter, J. Org. Chem. 53, 1026 (1988) and references cited therein.CrossRefGoogle Scholar
  49. 40.
    R. Franz, J. Fluorine Chem. 15, 423 (1980).CrossRefGoogle Scholar
  50. 41.
    See, for example, A. D. Borthwick, S. Butt, K. Biggadike, A. M. Exall, S. M. Roberts, P. M. Youds, B. E. Kirk, B. R. Booth, J. M. Cameron, S. W Cox, C. L. P. Marr, and M. D. Shill, J. Chem. Soc, Chem. Commun. 656 (1988).Google Scholar
  51. 42.
    Yu. M. Pustovit and V. P. Nazaretian, J. Fluorine Chem. 55, 29 (1991).CrossRefGoogle Scholar
  52. 43.
    H. Suschitzky, in Ref. 14, Vol. 4, p. 1 (1965).Google Scholar
  53. 44.
    T. N. Wade, J. Org. Chem. 45, 5328 (1980)CrossRefGoogle Scholar
  54. T. N. Wade and R. Khéribet, J. Org. Chem. 45, 5333 (1980)CrossRefGoogle Scholar
  55. G. M. Lavernhe, C. M. Ennakoua, S. M. Lacombe, and A. J. Laurent, J. Org. Chem. 46, 4938 (1981).CrossRefGoogle Scholar
  56. 45.
    S. Rozen and C. Gal, J. Org. Chem. 52, 2769 (1987); 55, 2803 (1988)CrossRefGoogle Scholar
  57. S. Rozen, Acc. Chem. Res. 21, 307 (1988).CrossRefGoogle Scholar
  58. 46.
    V. Grakauskas, Intra-Sci. Chem. Rep. 5 (1), 85 (1971); J. Org. Chem. 35, 723 (1970).Google Scholar
  59. 47.
    S. Misaki, Chem. Express 1(11), 683 (1986).Google Scholar
  60. 48.
    S. T. Purrington and D. L. Woodard, J. Org. Chem. 56, 142 (1991).CrossRefGoogle Scholar
  61. 49.
    R. Chirakal, E. S. Garnett, G. J. Schrobilgen, C. Nahmias, and G. Firnau, Chem. Br. 27, 47 (1991).Google Scholar
  62. 50.
    F. M. Mukhametshin, in Ref. 3, p. 69.Google Scholar
  63. 51.
    G. G. Furin, in Ref. 3, p. 35.Google Scholar
  64. 52.
    V. V. Bardin and Y. L. Yagupolskii, in Ref. 3, p. 1.Google Scholar
  65. 53.
    E. Differding and H. Ofner, Synlett. 187, 395 (1991)CrossRefGoogle Scholar
  66. F. A. Davis and W. Han, Tetrahedron Lett. 32, 1631 (1991).CrossRefGoogle Scholar
  67. 54.
    R. E. Banks, S. N. Mohialdin-Khaffaf, G. S. Lal, I. Sharif, and R. G. Syvret, J. Chem. Soc, Chem. Commun. 595 (1992).Google Scholar
  68. 55.
    Y. Takeuchi, K. Nagara, and R. Koizumi, J. Org. Chem. 52, 5062 (1987).CrossRefGoogle Scholar
  69. 56.
    Z-.Q. Xu, D. D. Desmarteau, and Y. Gotoh, J. Chem. Soc, Chem. Commun, 179 (1991).Google Scholar
  70. 57.
    I. N. Rozhkov, Russ. Chem. Rev. 45, 615 (1976).CrossRefGoogle Scholar
  71. 58.
    J. H. H. Meurs, D. W. Sopher, and W. Eilenberg, Angew. Chem., Int. Ed. Engl 28, 927 (1989)CrossRefGoogle Scholar
  72. J. H. H. Meurs and W. Eilenberg, Tetrahedron 47, 705 (1991).CrossRefGoogle Scholar
  73. 59.
    A. J. Woytek, in Ref. 7, p. 331.Google Scholar
  74. 60.
    B. D. Joyner, in Ref. 7, p. 337.Google Scholar

Copyright information

© Springer Science+Business Media New York 1994

Authors and Affiliations

  • R. E. Banks
    • 1
  • J. C. Tatlow
    • 2
  1. 1.Department of ChemistryThe University of Manchester Institute of Science and TechnologyManchesterEngland
  2. 2.Editorial Office of the Journal of Fluorine ChemistryBirminghamEngland

Personalised recommendations