Fluorination of aromatic compounds by halogen exchange with fluoride anions ("halex" reaction)

Industrial Chemistry Library

Volumn 8, Issue C, 1996, Pages 244-292

  Langlois, Bernard ^a   Gilbert, Laurent ^b   Forat, Gerard ^b  

^a UNIVERSITÉ LYON 1   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001135885     PISSN: 09269614     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0926-9614(96)80019-0     Document Type: Article

References (73)

1. Gottlieb H.B. J. Am. Chem. Soc. 58 (1936) 532
2. Cox D.P., Terpinski J., and Lawrynowicz W. J. Org. Chem. 49 (1984) 3216
3. Clark J.H., and Smith D.K. Tetrahedron Lett. 26 (1985) 2233
4. Finger G.C., and Kruse C.W. J. Am. Chem. Soc. 78 (1956) 6034
5. Prescott W. Chem. & Ind. (1978) 56
6. de Nie-Sarink M.J., and Prillwitz P.E. Speciality Chemicals (1984) 9
7. Bunnett J.F., and Morath R.J. J. Am. Chem. Soc. 77 (1955) 5051
8. Bunnett J.F., and Morath R.J. J. Am. Chem. Soc. 77 (1955) 5055
9. Starr L.D., and Finger G.C. Chem. & Ind. (1962) 1328
10. Clark J.H., Robertson M.S., Smith D.K., Cook A., and Streich C. J. Fluorine Chem. 28 (1985) 161
11. Finger G.C., Starr L.D., Dickerson D.R., Gutowsky H.S., and Hamer J. J. Org. Chem. 28 (1963) 1666
12. Dolby-Glover L. Chem & Ind. (1986) 518
13. Clark J.H., and Macquarrie D. J. Fluorine Chem. 35 (1987) 591
14. Asquit R.S., Lord W.M., Peters A.T., and Wallace F. J. Chem. Soc. (C) (1966) 95
15. Morgan S.E., Rackham D.M., Swann B.P., and Turner S.P. Tetrahedron Lett. 48 (1978) 4837
16. Finger G.C., Dickerson D.R., and Shiley R. J. Fluorine Chem. 1 (1972) 415
17. Yakobson G.G., and Akhmetova N.E. Synthesis (1983) 169
18. (supported by Rhône-Poulenc Co.). Rieux C. PhD dissertation (1989), University of Aix-Marseille III (France)
19. série II. Rieux C., Langlois B., and Gallo R. C.R. Acad. Sci. Paris 310 (1990) 25
20. Albert P., and Cousseau J. J. Chem. Soc., Chem. Commun. (1985) 961
21. P. Albert, J. Cousseau, PCT Int. Appl. WO 86/00,294, (1984). [Chem. Abstr., 105, 225755].
22. Roshchupkina C.S., Goldenberg L.M., and Lyubovskaya R.N. Koord. Khim. 13 (1987) 1242
23. Bosch P., Camps F., Chamorro E., Gasol V., and Guerrero A. Tetrahedron Lett. 28 (1987) 4733
24. Brown S.J., and Clark J.H. J. Fluorine Chem. 30 (1985) 251
25. S.J. Brown, J.H. Clark, E. P. 187,023 (to I.C.I. PLC Ltd.) (1985).
26. Cainelli G., Manescalchi F., and Panunzio M. Synthesis (1976) 472
27. Colonna S., Re A., Gelbard G., and Cesarotti E. J. Chem. Soc., Perkin Trans. I (1979) 2248
28. Urata Y. Memoirs of the Defence Academy, Japan 14 1 (1974) 13
29. Gutmann V. Angew. Chem. Int. Ed. Engl. 9 (1970) 843
30. Reichardt C. Solvents and Solvent Effects in Organic Chemistry. 2nd ed. (1988), Verlag Chemie, Weiheim
31. Pr. Phan-Tan-Luu, University of Aix-Marseille III, France.
32. Handbook of Chemistry and Physics. 65th ed. (1984), CRC Press
33. Wallenfels K., and Draber W. Chem. Ber. 90 (1957) 2819
34. Woyski M.M. J. Am. Chem. Soc. 52 (1950) 919
35. C.R. White, U.S. 4,642,399 (to Mallinckrodt Inc.), (1984).
36. Dermick P., and Sasson Y. J. Fluorine Chem. 22 (1983) 431
37. R.A. North, DE 2,938,939 (to Boots Co. Ltd.), (1978).
38. DE 1,949,424 (1968), (to ICI Ltd).
39. BE 768,204 (1970), (to ICI Ltd).
40. R.D. Bowden, M.B. Green, A. Nicolson, GB 1,306,596, (1970) (to I.C.I. Ltd.).
41. D.W. Headford, J.W. Slater, R.L. Sunley, R.D. Bowden, M.B. Green, DE 2,425,239? (1973), (to I.C.I. Ltd.).
42. Smyth T.P., Carey A., and Hodnett B.K. Tetrahedron 51 22 (1995) 6363
43. Clark J.H., and Macquarrie D.J. Tetrahedron Lett. 28 (1987) 111
44. Yoshida Y., and Kimura Y. Chem. Lett. (1988) 1355
45. Yoshida Y., and Kimura Y. J. Fluorine Chem. 44 (1989) 291
46. Y. Yoshida, Y. Kimura, JP J 63 170,332, (1989), (to Ihara Chem. Ind. Co.) [Chem. Abstrt., 109, 230540].
47. H. Ito, V. Matsushita, T. Shimizu, N. Ishikawa, M. Shimizu, EP 259,663, (1986), (to SDS Biotech. K.K.) [Chem. Abstr. 109, 128588].
48. H. Momotake, JP 63, 284, 135A2, (1987), (to Mitsui Toatsu Chemicals Inc.), [Chem. Abstr., 110, 134341].
49. R.A. North, GB 2,042,507, (1979), (to Boots Co. Ltd).
50. C.R. White, U.S. 4,418,229, (1981), (to Mallinckrodt Inc.).
51. Brunelle D.J., and Singleton D.A. Tetrahedron Lett. 25 (1984) 3383
52. G.L. Cantrell, PCT Int. Appl. WO 87/04148, WO 87/04149 and WO 87/04150, (1986), (to Mallinckrodt Inc.).
53. Yoshida Y., and Kimura Y. Tetrahedron Lett. 30 (1989) 7199
54. G.L. Cantrell, U.S. 4,642,398, (1986), (to Mallinckrodt Inc.).
55. R.A. Kuntz, U.S. 4,069,262, (1978), (to Du Pont de Nemours Co.) [Chem. Abstr., 88, 120762].
56. J. Maul, D. Tang, ED 180,057, (1984), (to Occidental Chem. Co.).
57. S. Kumai, M. Sasabe, H. Matsuo, Japan. Kokai JP 60 228,436, (1984), (to Asahi Glass Co.) S. Kumai, M. Sasabe, H. Matsuo, Japan Pat. JP 85,228,436 (1984); S. Kumai, M. Sasabe, H. Matsuo, Japan Kokai JP 60 246,326 and Japan. Pat. JP 85, 246,326 (1984).
58. T.J. Giacobbe, U.S. 4,031,100, (1976), (to Dow Chem. Co.).
59. Jeanne F., and Trichet A. Informations Chimie 155 (1976) 327
60. Aksenov V.V., Platonov V.M., Moryakina I.M., Rodionov P.P., and Fadeeva V.P. Izv. Akad Nauk SSSR, Ser. Khim. (1987) 690
61. Y. Yoshida, Y. Kimura, Japan. Kokai JP 63 170,332, (1986), (to Ihara Chem. Ind. Co.) [Chem. Abstr. 109, 230540]; Y. Yoshida, Y. Kimura, EP 289,942, (1988) (to Ihara Chem. Ind. Co.).
62. G. Soula, R. Ramanadin, M. Roustan, EP 32,077, (1979), (to Rhône-Poulenc); G. Soula, R. Ramanadin, M. Roustan, EP 49,186, (1980), (to Rhône-Poulenc).
63. Kitazume T., and Ishikawa N. Chem. Lett. (1978) 283
64. S. Kumai, T. Seki, H. Matsuo, JP 60 237,051, (1984), (to Asahi Glass Co.).
65. I.S.C. Chem Ltd., DE 2,527,944, (1974), (to I.S.C. Chem. Ltd)
66. B. Langlois, L. Gilbert, G. Forat, FR 2,664,590, (1990), (to Rhône-Poulenc Chimie).
67. J.M. Grosselin, R. Baillard, G. Cordier, B. Langlois, L. Gilbert, G. Forat, EP 409,709, (1990), (to Rhône-Poulenc Chimie).
68. G. Forat, L. Gilbert, B. Langlois, EP 467,742, (1991), (to Rhône-Poulenc Chimie).
69. Ishikawa N., Kitazume T., Yamazaki T., Mochida Y., and Tasumo T. Chem. Lett. (1981) 761
70. K. Suzuki, S. Hiyama and M. Ohashi, JP 63 010,737, (1986), (to Seimi Chem. Co.), [Chem. Abstr., 109, 73124].
71. Kimura Y., and Suzuki H. Tetrahedron Lett. 30 (1989) 1271
72. N. Miki, U.S. 4,806,332, (1987), (to Hashimoto Chem. Ind. Co.), [Chem. Abstr., 110, 195823].
73. Dermeik S., and Sasson Y. J. Org. Chem. 50 (1985) 879