Selectfluor™ reagent F-TEDA-BF4 in action: Tamed fluorine at your service

Journal of Fluorine Chemistry

Volumn 87, Issue 1, 1998, Pages 1-17

  Banks, Ronald Eric ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

1 Chloromethyl 4 fluoro 1,4 diazoniabicyclo 2.2.2 octane bis(tetrafluoroborate); Electrophilic fluorination; F TEDA BF4; Fluorinated biochemicals; N fluoro compounds

Indexed keywords

EID: 0032472096     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(97)00127-9     Document Type: Review

References (87)

1. [1] R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994.
2. [2] R.E. Banks, Fluorine the enabler, in: R.E. Banks, K.C. Lowe, Fluorine in Medicine in the 21st Century, Paper 1, Chemserve (UMIST), Manchester, 1994.
3. [3] R.E. Banks, Fluorine the superhalogen, in: R.E. Banks (Ed.), Fluorine in Agriculture, Paper 1, Fluorine Technology, Manchester, 1995.
4. [4] B.E. Smart, Characteristics of C-F systems, in: R.E. Banks, B.E. Smart, J.C. Tatlow, Plenum, New York, 1994, pp. 57-88.
5. [5] A. Bondi, J. Phys. Chem. 68 (1964) 441.
6. [6] A.V. Grosse, G.H. Cady, Ind. Eng. Chem. 39 (1947) 367.
7. [7] J.B.A. Dumas, E.M. Péligot, Ann. Pharm. 15 (1835) 246.
8. [8] J.B.A. Dumas, E.M. Péligot, Ann. Chim. Phys. 61 (1836) 193.
9. [9] R.E. Banks, J.C. Tatlow, Organofluorine chemistry: nomenclature and historical landmarks. R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994, pp. 1-24.
10. [10] J.A. Wilkinson, Chem. Rev. 92 (1992) 505.
11. [11] M. Meyer, D. O'Hagan, Chem. in Brit. 28 (1992) 785.
12. [12] Climate Change 1995: IPCC Summary for Policymakers and Technical Summary of the Working Group I Report, WMO/UNEP.
13. [13] J. Harnisch, R. Borchers, P. Fabian, H.W. Gäggeler, U. Schotterer, Nature, 384 (1996) 32.
14. [14] R.E. Banks, J.C. Tatlow, Synthesis of organofluorine compounds, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994, pp. 25-55.
15. [15] P.N. Edwards, Uses of fluorine in chemotherapy, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994, pp. 501-541.
16. [16] R. Filler, Y. Kobayashi, L.M. Yagupolski (Eds.), Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993.
17. [17] R.E. Banks, K.C. Lowe (Eds.), Fluorine in Medicine in the 21st Century, Chemserve (UMIST), Manchester, 1994.
18. [18] A. Becker, Inventory of Industrial Fluoro-Biochemicals, Eyrolles, Paris, 1996.
19. [19] R.E. Banks (Ed.), Fluorine in Agriculture, Fluorine Technology, Manchester, 1995.
20. [20] D. Cartwright, Recent developments in fluorine-containing agrochemicals', in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994, pp. 237-262.
21. 2 and some reagents directly derived from it, in: G.A. Olah, R.D. Chambers, G.K.S. Prakash (Eds.), Synthetic Fluorine Chemistry, Wiley, New York, 1992, pp. 143-161.
22. [22] A.B. McElroy, Applications of Fluorine in Medicinal Chemistry, in: R.E. Banks, K.C. Lowe (Eds.), Fluorine in Medicine in the 21st Century, Chemserve (UMIST), Manchester, 1994, paper 4.
23. [23] E. von Meyer, A History of Chemistry, (G. McGowan, Trans.), Macmillan, London, 1906.
24. [24] R.D. Chambers, M.P. Greenhall, J. Hutchinson, J. Tetrahedron 52 (1996) 1.
25. [25] R.D. Chambers, J. Hutchinson, J. Thomson, J. Fluorine Chem. 78 (1996) 165.
26. [26] R.D. Chambers, C.J. Skinner, J. Hutchinson, J. Thomson, J. Chem. Soc., Perkin Trans. 1, 605 (1996).
27. [27] J.R. Barrio, M. Namavari, M.E. Phelps, N. Satyamurthy, J. Am. Chem. Soc. 118 (1996) 10408.
28. [28] R.D. Bowden, J.S. Moilliet, Fluorine - a beast no more?, Speciality Chemicals Vol. 16, 8, 1996, pp. 284, 286, 288, 290.
29. [29] F.M. Mukhametshin, Hypofluorites and their application in organic synthesis, in: L.S. German, S.V. Zemskov (Eds.), New Fluorinating Agents in Organic Synthesis, Springer-Verlag, Berlin, 1989, pp. 69-116.
30. [30] S. Rozen, Chem. Rev. 96 (1996) 1717.
31. [31] M.A. Tuis, Tetrahedron 51 (1995) 6605-6634.
32. [32] R.G. Syvret, Perchloryl fluoride, in: L.A. Paquette et al. (Eds.), Encyclopedia of Reagents for Organic Synthesis, Vol. 6, Wiley, New York, 1995, pp. 3939-3942.
33. [33] N.S. Zefirov, Cesium fluoroxysulfate, L.A. Paquett et al. (Eds.), Encyclopedia of Reagents for Organic Synthesis, Vol. 2, Wiley, New York, 1995, pp. 1046-1048.
34. [34] G.S. Lal, G.P. Pez, R.G. Syvret, Chem. Rev. 96 (1996) 1737.
35. [35] V.V. Bardin, Y.L. Yagupolskii, Xenon difluoride, in: L.S. German, S.V. Zemskov (Eds.), New Fluorinating Agents in Organic Synthesis, Springer-Verlag, Berlin, 1989, pp. 1-34.
36. [36] G.G. Furin, Some electrophilic fluorination agents, in: L.S. German, S.V. Zemskov (Eds.), New Fluorinating Agents in Organic Synthesis, Springer-Verlag, Berlin, 1989, pp. 35-68.
37. [37] R.E. Banks, G.E. Williamson, Chem. Ind. (London), (1964) 1864.
38. [38] C.M. Sharts, W.A. Sheppard, Org. React. 21 (1974) 125.
39. 8, J. Chem. Soc., Perkin Trans. 1 (1972) 1098.
40. [40] R.E. Banks, Fluorocarbon and related chemistry, in: R.E. Banks, M.G. Barlow (Eds.), Royal Society of Chemistry Specialist Periodical Report, Vol. 2, 1974, p. 206.
41. [41] R.E. Banks, V. Murtagh, E. Tsiliopoulos, J. Fluorine Chem. 52 (1991) 389.
42. [42] R.E. Banks, I. Sharif, J. Fluorine Chem. 55 (1991) 207.
43. [43] R.E. Banks, M.K. Besheesh, J. Fluorine Chem. 76 (1996) 161.
44. [44] R.E. Banks, V. Murtagh, in: L.A. Paquette et al. (Eds.), Encyclopedia of Reagents for Organic Synthesis, Vol. 6, Wiley. Chichester, 1995, p. 3942.
45. [45] S.T. Purrington, W.A. Jones, J. Org. Chem. 48 (1983) 761.
46. [46] W.E. Barnette, J. Am. Chem. Soc. 106 (1984) 452.
47. [47] T. Umemoto, K. Tomita, Tetrahedron Lett. 27 (1986) 3271.
48. [48] T. Umemoto, K. Kawada, K. Tomita, Tetrahedron Lett. 27 (1986) 4465.
49. [49] R.E. Banks, R.A. Du Boisson, E. Tsiliopoulos, J. Fluorine Chem. 32 (1986) 461.
50. [50] D.D. DesMarteau, USP 4,697,011/1987.
51. [51] R.E. Banks, R.A. Du Boisson, W.D. Morton, E. Tsiliopoulos, J. Chem. Soc., Perkin Trans, 1 (1988) 2805.
52. [52] R.E. Banks, M.K. Besheesh, J. Fluorine Chem. 74 (1995) 165.
53. [53] T. Umemoto, M. Nagayoshi, Bull. Chem. Soc. Jpn. 69 (1996) 2287.
54. [54] R.E. Banks, M.K. Beshesh, I. Sharif, publication in preparation.
55. [55] R.E. Banks, USP 5,086,178/1992 (to Air Products and Chemicals).
56. [56] R.E. Banks, M.K. Besheesh, S.N. Mohialdin-Khaffaf, I. Sharif, J. Fluorine Chem. 78 (1996) 43.
57. [57] R.E. Banks, M.K. Besheesh, S.N. Mohialdin-Khaffaf, I. Sharif, J. Chem. Soc., Perkin Trans. 1 (1996) 2069.
58. [58] A.G. Gilicinski, G.P. Pez, R.G. Syvret, G.S. Lal, J. Fluorine Chem. 59 (1992) 157.
59. [59] M. Abdul-Ghani, R.E. Banks, M.K. Besheesh, I. Sharif, R.G. Syvret, J. Fluorine Chem. 73 (1995) 255.
60. [60] D.L. Illman, Chem. Eng. News. (Science/Technology Section) 71 (36) (1993) 26.
61. [61] G.P. Pez, Harnessing fluorine for pharmaceuticals, Air Products Technology Impact Magazine, Vol. No. 3, Oct. 1993, pp. 2-9.
62. [62] R.E. Banks, V. Murtagh, in: L.A. Paquette et al. (Eds.), Encyclopedia of Reagents for Organic Synthesis, Vol. 2. Wiley, Chichester, 1995, pp. 1150-1153.
63. [63] R.E. Banks, I. Sharif, R.G. Pritchard, Acta Crystallogr. C49 (1993) 492.
64. 4): A new broad-spectrum selective fluorinating agent, in: R.E. Banks (Ed.), Fluorine in Agriculture, Paper 16, Fluorine Technology, Manchester, 1995.
65. [65] G.S. Lal, J. Org. Chem. 58 (1993) 2791.
66. [66] M. Zupan, J. Iskra, S. Stavber, J. Fluorine Chem. 70 (1995) 7.
67. [67] M. Zupan, J. Iskra, S. Stavber, Tetrahedron 52 (1996) 11341.
68. [68] M. Zupan, J. Iskra, S. Stavber, Bull. Chem. Soc. Jpn. 68 (1995) 1655.
69. [69] M. Brunavs, C.P. Dell, M.W. Owton, J. Fluoriae Chem. 68 (1994) 201.
70. [70] G.S. Lal, W. Pastore, R. Pesaresi, J. Org. Chem. 60 (1995) 7340.
71. [71] G.S. Lal. Synth. Commun. 25 (1995) 725.
72. [72] J.Y. Godard, Strategies for introducing fluorine into corticosteroids, in: R.E. Banks (Ed.), Fluorine in Medicine in the 21st Century, Chemserve (UMIST), Manchester, 1994, paper 10.
73. [73] H.F. Hodson, D.J. Madge, D.A. Widdowson, J. Chem. Soc., Perkin Trans, 1 (1995) 2965.
74. [74] D.F. Mathews, S.C. Miller, E.T. Jarvi, J.S. Sabol, J.R. McCarthy, Tetrahedron Lett. 34 (1993) 3057.
75. [75] H.F. Hodson, D.J. Madge, A.N.Z. Slawin, D.A. Widdowson. D.J. Williams, Tetrahedron 50 (1994) 1899.
76. [76] M.A. McClinton, V. Sik, J. Chem. Soc., Perkin Trans. 1 (1992) 1891.
77. [77] R.E. Banks, N.J. Lawrence, M.K. Besheesh, A.L. Popplewell, R.G. Pritchard, J. Chem. Soc., Chem. Commun., (1996) 1629.
78. [78] R.E. Banks, N.J. Lawrence, A.L. Popplewell, Synlett., (1994) 831.
79. [79] A.K. Forrest, P.J. O'Hanlon, Tetrahedron Lett. 36 (1995) 2117.
80. [80] J. Wang. A.I. Scott, J. Chem. Soc., Chem. Commun., (1995) 2399.
81. [81] R.E. Banks, N.J. Lawrence, A.L. Popplewell, J. Chem. Soc., Chem. Commun., (1994) 343.
82. [82] D.S. Brown, B.A. Marples, P. Smith, L. Walton, Tetrahedron 51 (1995) 3587.
83. [83] S. Stavber, T. Sotler, M. Zupan, Tetrahedron Lett. 35 (1994) 1105.
84. [84] M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259.
85. [85] S. Stavber, T. Sotler-Pecan, M. Zupan, Bull. Chem. Soc. Jpn. 69 (1996) 169.
86. [86] K. Westerman, H. Jiminez, R. Montano, P.E. Vorndam, M.L. Druelinger, Abstr. Papers Am. Chem. Soc. 209 (1) (1995) 242-CHED.
87. [87] S. Stavber, T.S. Pecan, M. Papez, M. Zupan, J. Chem. Soc., Chem. Commun., (1996) 2247.