N-halogeno compounds. Part 18. 1-Alkyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octane salts: User-friendly site-selective electrophilic fluorinating agents of the N-fluoroammonium class

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1996, Pages 2069-2076

  Banks, R Eric ^a   Besheesh, Mohamed K ^a   Mohialdin Khaffaf, Suad N ^a   Sharif, Iqbal ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748883587     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960002069     Document Type: Article

References (72)

1. Preliminary communication: R. E. Banks, S. N. Mohialdin-Khaffaf, G. S. Lal, I. Sharif and R. G. Syvret, J. Chetn. Soc., Chem. Commun., 1992, 595.
2. Oral presentation: R. E. Banks, Plenary Lecture ('In search of user-friendly cost-effective electrophilic fluorinating agents of the NF class'), at the ACS 11th Winter Fluorine Conference, St. Petersburg, Florida, 1993 (abstract 1).
3. (a) R. E. Banks and J. C. Tatlow, in Organofluorine Chemistry: Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York and London 1994, pp. 25-55, ch. 2;
4. (b) J. A. Wilkinson, Chem. Rev., 1992, 92, 505;
5. O. A. Mascaretti, Aldrichimica Acta, 1993, 26 (2), 47;
6. (c) T. Umemoto, in Reviews on Heteroatom Chemistry, ed. S. Oae, A. Ohno and T. Okuyama, MYU, Tokyo, 1994, vol. 10, pp. 123-154.
7. B. K. Bennett, R. G. Harrison and T. G. Richmond, J Am Chem. Soc., 1994, 116, 11165;
8. R. D. Chambers, S. R. Korn and G. Sandford, J. Fluorine Chem., 1994, 69, 103.
9. M. R. Kilbourn, Fluorine-18 Labelling of Radiopharmaceuticals, National Academy Press, Washington, D. C., 1990;
10. 'Fluorine-18 in Nuclear Medicine', in Fluorine in Medicine in the 21st Century, ed. R. E. Banks and K. C. Lowe, Chemserve (UMIST), Manchester 1994, paper 12.
11. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, ed. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Elsevier, Amsterdam, 1993;
12. Fluorine in Medicine in the 21st Century, ed. R. E. Banks and K. C. Lowe, Chemserve (UMIST), Manchester, 1994;
13. Fluorine in Agriculture, ed. R. E. Banks, Fluorine Technology Ltd., Manchester, 1994;
14. P. N. Edwards, 'Uses of Fluorine in Chemotherapy', in ref. 2(a), pp. 501-554;
15. D. Cartwright, 'Recent Developments in Fluorine-containing Agrochemicals', in ref. 2(a), pp. 237-262;
16. D. F. Halpern, 'Fluorinated Inhalation Anesthetics', in ref. 2(a), pp. 543-554.
17. R. E. Banks and J. C. Tatlow, J. Fluorine Chem., 1986, 33, 227.
18. R. E. Banks and G. E. Williamson, Chem. Ind. (London), 1964, 1864.
19. S. T. Purrington and W. A. Jones, J. Org. Chem., 1983, 48, 761.
20. W. E. Barnette, J. Am. Chem. Soc., 1984, 106, 452.
21. A. G. Gilicinski, G. P. Pez, R. G. Syvret and G. S. Lal, J. Fluorine Chem., 1992, 59, 157.
22. T. Umemoto and K. Tomita, Tetrahedron Lett., 1986, 27, 3271;
23. T. Umemoto, K. Kawada and K. Tomita, Tetrahedron Lett., 1986, 27, 4465.
24. (For more detailed accounts, see T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada and K. Tomita, J. Am. Chem. Soc., 1990, 112, 8563;
25. T. Umemoto, K. Harasawa, G. Tomizawa, K. Kawada and K. Tomita, Bull. Chem. Soc. Jpn., 1991, 64, 1081.)
26. R. E. Banks, R. A. Du Boisson and E. Tsiliopoulos, J. Fluorine Chem. 1986, 32, 461.
27. D. D. DesMarteau, USP 4,697,011/1987 and 4,828,764/1989;
28. S. Singh, D. D. DesMarteau, S. S. Zuberi, M. Witz and H.-N. Huang, J. Am. Chem. Soc., 1987, 109, 7194.
29. See, for example, the catalogue Fluorinated Products from Aldrich (1995-1996), p. 172;
30. Fluorinating Agents and Naked Fluorides, Fluka Chemika News '95 (November).
31. R. E. Banks, USP 5,086,178/1992 (to Air Products & Chemicals, Inc.).
32. (a) D. L. Illman, Chem. Eng. News (Science/Technology section), 1993, 71 (36), 26;
33. G. P. Pez, 'Harnessing Fluorine for Pharmaceuticals', Air Products Technology Impact Magazine, October 1993, No. 3, pp. 2-9;
34. (b) An MSDS (Material Safety Data Sheet) and samples or test quantities are available from either Dr Reiner Taege, c/o Air Products PLC, European Technology Group, Chineham, Basingstoke, Hampshire, RG24 8FE, UK, or Dr Guido P. Pez, Chief Scientist (Inorganic Chemistry), Air Products & Chemicals, Inc., 7201 Hamilton Boulevard, Allentown, PA 18195-1501, USA.
35. For further details, see the article 'Selectfluor™' by R. E. Banks, in UMIST Research Focus, 1994, No. 3, pp. 1 and 4 (available from the Information Office, UMIST, Manchester M60 1QD, UK).
36. R. E. Banks, R. A. Du Boisson, W. D. Morton and E. Tsiliopoulos, J. Chem. Soc., Perkin Trans. 1, 1988, 2805.
37. (a) R. E. Banks and I. Sharif, J. Fluorine Chem., 1991, 55, 207;
38. (b) R. E. Banks and M. K. Besheesh, J. Fluorine Chem., 1996, 76, 161.
39. E. Tsiliopoulos, Ph.D. Thesis, University of Manchester, UK, 1986;
40. I. Sharif, Ph.D. Thesis, University of Manchester, UK, 1992;
41. R. E. Banks and S. N. Mohialdin-Khaffaf, unpublished results.
42. R. E. Banks and M. K. Besheesh, J. Fluorine Chem., 1995, 74, 165.
43. R. E. Banks, M. K. Besheesh, S. N. Mohialdin-Khaffaf and I. Sharif, J. Fluorine Chem., 1996, 78, 43.
44. (a) R. E. Banks and V. Murtagh, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 2;
45. (b) G. S. Lal, in Fluorine in Agriculture, ed. R. E. Banks, Fluorine Technology Ltd., Manchester, 1995, paper 16.
46. For a review see G. S. Lal, G. P. Pez and R. G. Syvret, Chem. Rev., 1996, in the press (we are indebted to Dr Pez for providing us with a copy of the manuscript).
47. Note that the most incisive investigations have been carried out by Differding et al., E. Differding and G. M. Rüegg, Tetrahedron Lett., 1991, 32, 3815;
48. E. Differding and M. Wehrli, Tetrahedron Lett., 1991, 32, 3819;
49. E. Differding and P. M. Bersier, Tetrahedron, 1992, 48, 1595;
50. C. P. Andrieux, E. Differding, M. Robert and J.-M. Savéant, J. Am. Chem. Soc., 1993, 115, 6592.
51. See also F. A. Davis, W. Han and C. K. Murphy, J. Org. Chem., 1995, 60, 4730.
52. First disclosed orally at the international symposium Centenaire de la Decouverte du Fluor, Paris, France, 25 Aug. 1986 (abstract 07;
53. see J. Fluorine Chem., 1987, 35, 13).
54. See also R. E. Banks, in Fluorocarbon and Related Chemistry, Royal Society of Chemistry Specialist Periodical Report Series, 1974, vol. 2, p. 206.
55. R. E. Banks, V. Murtagh and E. Tsiliopoulos, J. Fluorine Chem., 1991, 52, 389.
56. M. Abdul-Ghani, R. E. Banks, M. K. Besheesh, I. Sharif and R. G. Syvret, J Fluorine Chem., 1995, 73, 255.
57. G. S. Lal, J. Org. Chem., 1993, 58, 2791.
58. S. Stavber, T. Sotler and M. Zupan, Tetrahedron Lett., 1994, 35, 1105.
59. M. Zupan, J. Iskra and S. Stavber, J. Org. Chem., 1995, 60, 259.
60. R. E. Banks, N. J. Lawrence and A. L. Popplewell, J. Chem. Soc., Chem. Commun., 1994, 343.
61. D. S. Brown, B. A. Marples, P. Smith and L. Walton, Tetrahedron, 1995, 51, 3587.
62. G. S. Lal, W. Pastore and R. Pesaresi, J. Org. Chem., 1995, 60, 7340.
63. G. S. Lal, Synth. Commun., 1995, 25, 725.
64. M. Brunavs, C. P. Dell and W. M. Owton, J. Fluorine Chem., 1994, 68, 201.
65. D. P. Matthews, S. C. Miller, E. T. Jarvi, J. S. Sabol and J. R. McCarthy, Tetrahedron Lett., 1993, 34, 3057.
66. H. F. Hodson, D. J. Madge, A. N. Z. Slawin, D. A. Widdowson and D. J. Williams, Tetrahedron, 1994, 50, 1899.
67. M. A. McClinton and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1992, 1891.
68. R. E. Banks, S. N. Mohialdin-Khaffaf, N. J. Lawrence and A. L. Popplewell, unpublished results.
69. R. E. Banks, N. J. Lawrence and A. L. Popplewell, unpublished observations.
70. R. E. Banks, R. N. Haszeldine and J. P. Lalu, J. Chem. Soc. (C), 1966, 1514.
71. R. E. Banks, J. Fluorine Chem., 1986, 33, 3.
72. R. E. Banks, S. N. Mohialdin-Khaffaf and R. G. Pritchard, unpublished results.