Nucleophilic reactivity towards electrophilic fluorinating agents: Reaction with N-fluorobenzenesulfonimide ((PhSO2)2NF)

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 10, 2000, Pages 2071-2076

  Antelo, Juan M ^a   Crugeiras, Juan ^a   Leis, J Ramón ^a   Ríos, Ana ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CHEMICAL ANALYSIS; ELECTRON TRANSPORT PROPERTIES; FLUORINE; IONIC STRENGTH; NITROGEN; OXIDATION; OXYGEN; RATE CONSTANTS; SOLUTIONS; SULFUR; SYNTHESIS (CHEMICAL);

ELECTRPHILIC FLUORINATING AGENTS; N-FLUOROBENZENESULFONIMIDE; NUCLEOPHILIC REACTIVITY; ONE-ELECTRON TRANSFER;

FLUORINE COMPOUNDS;

EID: 0034309258     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003982i     Document Type: Article

References (40)

1. Biomedicinal Aspects of Fluorine Chemistry, eds. R. Filler and Y. Kobayashi, Elsevier Biomedical Press, New York, 1982.
2. M. R. C. Gerstenberger and A. Haas, Angew. Chem., Int. Ed. Engl., 1981, 20, 647.
3. J. T. Welch, Tetrahedron, 1987, 43, 3123.
4. G. S. Lal, G. P. Pez and R. G. Syvret, Chem. Rev., 1996, 96, 1737.
5. T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada and K. Tomita, J. Am. Chem. Soc., 1990, 112, 8563.
6. D. D. DesMarteau, Z. Xu and M. Witz, J. Org. Chem., 1992, 57, 629.
7. E. Differding and G. M. Rüegg, Tetrahedron Lett., 1991, 32, 3815.
8. E. Differding and M. Wehrli, Tetrahedron Lett., 1991, 32, 3819.
9. H. M. Teeter and E. W. Bell, Org. Synth., 1963, Coll. Vol. IV, 125.
10. M. D. Rosa and V. R. Marwaha, Heterocycles, 1994, 37, 979.
11. R. C. Troy, M. D. Kelley, J. C. Nagy and D. W. Margerum, Inorg. Chem., 1991, 30, 4838.
12. T. X. Wang, M. D. Kelley, J. N. Cooper, R. C. Beckwith and D. W. Margerum, Inorg. Chem., 1994, 33, 5872.
13. R. G. Pearson and J. Songstad, J. Am. Chem. Soc., 1967, 89, 1827.
14. G. Klopman, J. Am. Chem. Soc., 1968, 90, 223.
15. M. M. Cartwright and A. A. Woolf, J. Fluorine Chem., 1984, 25, 263.
16. K. O. Christe, J. Fluorine Chem., 1984, 25, 269.
17. C. P. Andrieux, E. Differding, M. Robert and J.-M. Savéant, J. Am. Chem. Soc., 1993, 115, 6592.
18. H. Lund and L. H. Kristensen, Acta Chem. Scand., Ser. B, 1979, 33, 495.
19. A. Pross, Acc. Chem. Res., 1985, 18, 212.
20. A. Pross and S. S. Shaik, Acc. Chem. Res., 1983, 16, 363.
21. H. Lund, K. Daasbjerg, T. Lund and S. U. Pedersen, Acc. Chem. Res., 1995, 28, 313.
22. S. Hoz, Acc. Chem. Res., 1993, 26, 69.
23. L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer-Verlag, Heidelberg, 1987.
24. E. Differding and H. Ofner, Synlett, 1991, 187.
25. E. Differding, R. O. Duthaler, A. Krieger, G. M. Rüegg and C. Schmidt, Synlett, 1991, 395.
26. C. G. Swain and C. B. Scott, J. Am. Chem. Soc., 1953, 75, 141.
27. R. G. Pearson, H. Sobel and J. Songstad, J. Am. Chem. Soc., 1968, 90, 319.
28. J. Koskikallio, Acta Chem. Scand., 1969, 23, 1477.
29. J. P. Richard, M. M. Toteva and J. Crugeiras, J. Am. Chem. Soc., 2000, 122, 1664.
30. C. D. Ritchie, Can. J. Chem., 1986, 64, 2239.
31. C. M. Gerritsen and D. W. Margerum, Inorg. Chem., 1990, 29, 2757.
32. P. R. Young and W. P. Jencks, J. Am. Chem. Soc., 1979, 101, 3288.
33. E. Buncel and H. Wilson, J. Chem. Edu., 1987, 64, 475.
34. R. A. M. O'Ferrall, J. Chem. Soc., (B), 1970, 274.
35. W. P. Jencks, J. Am. Chem. Soc., 1972, 72, 705.
36. C. D. Ritchie, J. Am. Chem. Soc., 1983, 105, 7313.
37. I. M. Gordon, H. Maskill and M. F. Ruasse, Chem. Soc. Rev., 1989, 18, 123.
38. J. L. Kice and E. Legan, J. Am. Chem. Soc., 1973, 95, 3912.
39. T. Deacon, A. Steltner and A. Williams, J. Chem. Soc., Perkin Trans. 2, 1975, 1778.
40. W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc., 1968, 90, 2622.