Stereochemistry and Some Kinetic Aspects of Fluorination of Phenyl-Substituted Alkenes with Selectfluor™ Reagent F-TEDA-BF4

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 1, 1996, Pages 169-175

  Stavber, Stojan ^a   Sotler Pečan, Tjaša ^a   Zupan, Marko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; FLUORINATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030048620     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.169     Document Type: Article

References (45)

1. For an extensive list of primary references see: a) T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada, and K. Tomita, J. Am. Chem. Sac., 112, 8563 (1990);
2. b) D. D. DesMarteau, Ze-Qi Xu, and M. Witz, J. Org. Chem., 57, 629 (1992);
3. c) G. Resnati and D. D. DesMarteau, J. Org. Chem., 57, 4281 (1992);
4. d) E. Differding and P. M. Bersier, Tetrahedron, 48, 1595 (1992).
5. a) "New Fluorinating Agents in Organic Syntheses," ed by L. German and S. Zemskov, Springer-Verlag, Berlin (1989); J. A. Wilkinson, Chem. Rev., 92, 505 (1992).
6. a) "New Fluorinating Agents in Organic Syntheses," ed by L. German and S. Zemskov, Springer-Verlag, Berlin (1989); J. A. Wilkinson, Chem. Rev., 92, 505 (1992).
7. a) J. T. Welch, Tetrahedron, 43, 3123 (1987);
8. b) J. Man, Chem. Soc. Rev., 16, 381 (1987);
9. c) J. T. Welch and S. Eswarakrishnan, "Fluorine in Biooganic Chemistry," Wiley, New York (1991);
10. "Organofluorine Compounds in Medicinal Chemistry and Biomedical Application," ed by R. Filler, Y. Kobayashi, and L. M. Yagupolskii, Elsevier, Amsterdam (1993).
11. R. E. Banks, U. S. Patent 5086178 (1992); (produced by Air Products and Chemicals, Inc.).
12. R. E. Banks, S. N. Mohialdin-Khaffaf, G. S. Lal, I. Sharif, and R. R. Syvret, J. Chem. Soc., Chem. Commun., 1992, 595;
13. b) M. Zupan, J. Iskra, and S. Stavber, Bull. Chem. Soc. Jpn., 68, 1655 (1995); M. Zupan, J. Iskra, and S. Stavber, J. Fluorine Chem., 70, 7 (1995).
14. b) M. Zupan, J. Iskra, and S. Stavber, Bull. Chem. Soc. Jpn., 68, 1655 (1995); M. Zupan, J. Iskra, and S. Stavber, J. Fluorine Chem., 70, 7 (1995).
15. G. S. Lal, J. Org. Chem., 58, 2791 (1993).
16. S. Stavber, T. Sotler, and M. Zupan, Tetrahedron Lett., 35, 1105 (1994).
17. M. Zupan, J. Iskra, and S. Stavber, J. Org. Chem., 60, 259 (1995).
18. a) M. A. McClinton and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1992, 1891;
19. b) D. P. Matthews, S. C. Miller, E. T. Jarvi, J. S. Sabol, and J. R. McCarty, Tetrahedron Lett., 34, 3057 (1993).
20. R. E. Banks, N. J. Lawrence, and A. L. Popplewell, J. Chem. Soc., Chem. Commun., 1994, 343.
21. S. Stavber and M. Zupan, J. Chem. Soc., Chem. Commun., 1994, 149.
22. H. F. Hodson, D. J. Madge, A. N. Z. Slawin, and D. J. Widdowson, Tetrahedron, 50, 1899 (1994).
23. R. E. Banks, N. J. Lawrence, and A. L. Popplewell, Synlett, 1994, 831.
24. a) N. S. Levy and D. M. Sterling, J. Org. Chem., 50, 5615 (1985);
25. b) M. Zupan, M. Metelko, and S. Stavber, J. Chem. Soc., Perkin Trans. 1, 1993, 2851;
26. c) S. Stavber, T. Sotler M. Zupan, and A. Popovič, J. Org. Chem., 59, 5891 (1994);
27. d) S. Stavber, T. Sotler-Pečan, and M. Zupan, Tetrahedron, 50, 12235 (1994).
28. S. Stavber and M. Zupan, J. Org. Chem., 52, 919 (1987).
29. M. Zupan and A. Pollak, J. Org. Chem., 42, 1559 (1977).
30. D. H. R. Barton, R. H. Hesse, G. P. Jackman, L. Ogunkoya, and M. M. Pechet, J. Chem. Soc., Perkin Trans. 1, 1974, 739.
31. J. E. Dubois and A. F. Hegarty, J. Chem. Soc. B, 1969, 638.
32. F. Freeman, Chem. Rev., 75, 439 (1975).
33. D. J. Nelson, P. J. Cooper, and R. Soundararajan, J. Am. Chem. Soc., 111, 1414 (1989).
34. J. K. Kochi, Angew. Chem., 100, 1331 (1988).
35. H. C. Brown and Y. Okamoto, J. Am. Chem. Soc., 80, 4979 (1958).
36. K. O. Christe, J. Fluorine Chem., 25, 269 (1984).
37. a) O. Lerman, Y. Tor, D. Hebel, and S. Rosen, J. Org. Chem., 49, 806 (1984);
38. b) S. Rosen and R. Filler, Tetrahedron, 41, 1111 (1985).
39. G. M. B. Visser, S. Boele, B. W. van Halteren, G. H. J. N. Knopes, J. D. Hercheid, G. A. Brinkman, and A. Hoekstra, J. Org. Chem., 51, 1466 (1986).
40. E. Differding and M. Ruegg, Tetrahedron Lett., 32, 3815 (1991).
41. T. Iwaoka, C. Kaneko, A. Shigihara, and H. Ichikawa, J. Phys. Org. Chem., 6, 195 (1993).
42. C. P. Andieux, E. Differding, M. Robert, and J. M. Saveant, J. Am. Chem. Soc., 115, 6599 (1993).
43. R. E. Pearson and J. C. Martin, J. Am. Chem. Soc., 85, 3142 (1963).
44. C. K. Ingold and F. R. Shaw, J. Chem. Soc., 130, 2918 (1927).
45. S. Rosen and O. Lerman, J. Org. Chem., 45, 672 (1980).