Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane Salts (Selectfluor Reagents)

Journal of Organic Chemistry

Volumn 58, Issue 10, 1993, Pages 2791-2796

  Lal, G Sankar ^a  

^a AIR PRODUCTS AND CHEMICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000815463     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00062a023     Document Type: Article

References (40)

1. Fried, J.; Subo, E. F. J. Am. Chem. Soc. 1954, 1455.
2. Filler, R. Chem. Tech. 1974, 4, 752.
3. Filler, R., Kobayashi, Y., Eds.; Biomedical Aspects of Fluorine Chemistry; Elsevier Biomedicinal Press: New York, 1982.
4. Welch, J. T. Tetrahedron 1987, 43, 14, 3123.
5. German, L., Zemskov, S., Eds.; New Fluorinating Agents in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, 1989.
6. Sharts, C. M.; Sheppard, W. A. Org. React. 1974, 21, 225.
7. Mukametshin, F. M. Reference 4, pp 69–116.
8. Bardin, V. V.; Yagupolskii, Y. L. Reference 4, pp 1–34.
9. Murtagh, V. Perform. Chem. 1991, 6, 4, 36.
10. For an extensive, up-to-date list of primary references, see also: Banks, R. E.; Murtagh, V.; Tsiliopoulous, E. J. Fluorine Chem. 1991, 52, 389.
11. Resnati, G.; DesMarteau, D. D. J. Org. Chem. 1991, 56, 4925.
12. Banks, R. E. U.S. Patent, 5,086,178, 1992.
13. Gilicinski, A. G.; Pez, G. P.; Syvret, R. G.; Lal, G. S. J. Fluorine Chem. 1992, 59, 157.
14. Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, R. G. J. Chem. Soc., Chem. Commun. 1992, 595.
15. Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563.
16. Bailey, E. J.; Elks, J.; Oughton, J. F.; Stephenson, L. J. Am. Chem. Soc. 1961, 83, 4535.
17. Poss, A. J.; Van der Puy, M.; Nalewajek, D.; Shia, G. A.; Wagner, W. J.; Frenette, R. L. J. Org. Chem. 1991, 56, 5962.
18. Nakanishi, S.; Jensen, E. V. J. Org. Chem. 1962, 27, 702.
19. Zupan, M.; Pollak, A. J. Org. Chem. 1977, 42, 9, 1559.
20. Staver, S.; Zupan, M. Tetrahedron 1986, 42, 18, 5035.
21. DesMarteau, D. D.; Zu, Z. Q.; Witz, M. J. Org. Chem. 1992, 57, 629.
22. Rozen, S.; Lerman, O. J. Org. Chem. 1980, 45, 672.
23. Koizumi, T.; Hagi, T.; Horie, Y.; Takeuchi, Y. Chem. Pharm. Bull. 1987, 35, 3959.
24. Shaw, M. J.; Hyman, H. H.; Filler, R. J. Am. Chem. Soc. 1970, 92, 6498.
25. Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witz, M.; Hsu-Nan, H. J. Am. Chem. Soc. 1987, 109, 7194.
26. Stavber, S.; Zupan, M. J. Org. Chem. 1991, 56, 7347.
27. Sammes, P. G. Chem. Rev. 1976, 76, 113.
28. Hermann, P. Organic Sulfur Chemistry; Freidlima, R., Skorova, A. E., Eds.; Pergamon Press; Oxford, 1981; p 51.
29. Jarvi, E. T.; McCarthy, J. R.; Mehdi, S.; Matthews, D. P.; Edwards, M. L.; Prakash, N. J.; Bowlin, T. L.; Sunkara, P. S.; Bey, P. J. Med. Chem. 1991, 34, 647.
30. Zupan, M. J. Fluorine Chem. 1976, 8, 305.
31. Umemoto, T.; Tomizawa, G. Bull. Chem. Soc. Jpn. 1986, 59, 3625.
32. McCarthy, J. R.; Matthews, D. P.; Edwards, M. L.; Stemerik, D. M.; Jarvi, E. T. Tetrahedron Lett. 1990, 31, 38, 5449.
33. Takahara, T.; Shimokawa, K. Japan Patent, JP 59139398, Aug 10, 1984.
34. Takahara, T.; Shimokawa, K. U.S. Patent, 4,528,137, July 9, 1985.
35. Alvarez, F. S.; Prince, A. J. Org. Chem. 1972, 37, 18, 2920.
36. Zupan, M.; Pollak, A. J. Org. Chem. 1976, 41, 25, 4002.
37. Stavber, S. and Zupan, M. J. Org. Chem. 1987, 52, 919.
38. Rozen, S.; Lerman, O.; Kol, M.; Hebel, D. J. Org. Chem. 1985, 50, 4753.
39. Valkanas, G. J. Chem. Soc. 1963, 5554.
40. Klauke, E. U.S. Patent, 4,079,089, Mar 14, 1978.