Fluorination with XeF2. 44. Effect of geometry and heteroatom on the regioselectivity of fluorine introduction into an aromatic ring

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 878-880

  Zupan, Marko ^a   Iskra, Jernej ^a   Stavber, Stojan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000989473     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971496e     Document Type: Article

References (50)

1. For part 43, see: Stavber, S.; Koren, Z.; Zupan, M. Synlett 1994, 265.
2. (a) German, L.; Zemskov, S. New Fluorinating Agents in Organic Synthesis; Springer-Verlag: Berlin, 1989.
3. (b) Hudlicky, M.; Favlath, A. E., Eds. Chemistry of Organo Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1996.
4. (c) Clark, J. H.; Wails, D.; Bastock, T. W. Aromatic Fluorinations; CRC Press: New York, 1996.
5. Patai, S.; Rappoport, Z., Eds.; The Chemistry of Functional Groups, Supplement D2: The Chemistry of Halides, Psevdo-Halides and Azides, Part 1 and Part 2; Wiley: Chichester, 1995.
6. Zupan, M. Xenon Halide Halogenations, In The Chemistry of Functional Groups, Supplement D: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983.
7. Zupan, M. Functionalization of Organic Molecules by Xenon Fluorides. In The Chemistry of Functional Groups, Supplement D2: The Chemistry of Halides, Psevdo-Halides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1995.
8. Tius, M. A. Tetrahedron 1995, 51, 6605.
9. Shaw, M. J.; Weil, J. A.; Hyman, H. H.; Filler, R. J. Am. Chem. Soc. 1970, 92, 5096.
10. (a) Shaw, M. J.; Hyman, H. H.; Filler, R. J. Am. Chem. Soc. 1970, 92, 6498.
11. (b) Anand, S. P., Quarterman, L. A.; Hyman, H. H.; Migliorese, K. G.; Filler, R. J. Org. Chem. 1975, 40, 807.
12. Šket, B.; Zupan, M. J. Org. Chem. 1978, 43, 835.
13. Stavber, S.; Zupan, M. J. Org. Chem. 1983, 48, 2223.
14. Zupan, M.; Pollak, A. J. Org. Chem. 1975, 40, 3794.
15. Stavber, S.; Zupan, M. J. Chem. Soc., Chem. Commun. 1978, 969.
16. Stavber, S., Zupan, M. J. Org. Chem. 1981, 46, 300.
17. Frohn, H. J.; Bardin, V. V. J. Chem. Soc., Chem. Commun. 1993, 1072.
18. Zupan, M. Chimia 1976, 30, 305.
19. Taylor, R. Electrophilic Aromatic Substitution; Wiley: Chichester, 1990.
20. Sargent, M. V.; Stransky, P. O. Dibenzofurans. In Advances in Heterocyclic Chemistry, Vol. 35; Katritzky, A. R., Ed.; Academic Press: Orlando, 1984.
21. Traven, V. F. Frontier Orbitals and Properties of Organic Molecules; Ellis Horwood: New York, 1992.
22. Frank, N. L.; Siegel, J. S. Mills-Nixon Effects? In Advances in Theoretically Interesting Molecules, Vol. 3; JAI Press Inc.: Greenwich, 1995; p 209.
23. Eaborn, C.; Sperry, J. A. J. Chem. Soc. 1961, 4921.
24. Keumi, T.; Hamanaka, K.; Hasegawa, H.; Minamide, N.; Inoue, Y.; Kitajima, H. Chem. Lett. 1988, 1285.
25. Keumi, T.; Tomioka, N.; Hamanaka, K.; Kakihara, H.; Fukushima, M.; Morita, T.; Kitajima, H. J. Org. Chem. 1991, 56, 4671.
26. Eberson, L.; Radner, F. Acta Chem. Scand. 1992, 46, 312.
27. Eberson, L.; Hartshorn, M. P.; Radner, F.; Merchán, M.; Roos, B. O. Acta Chem. Scand. 1993, 47, 176.
28. Ohwada, T. J. Am. Chem. Soc. 1992, 114, 8818.
29. Zimmerman, U.-J. P.; Berliner, E. J. Am. Chem. Soc. 1962, 84, 3953.
30. Eberson, L.; Hartshorn, M. P.; Persson, O.; Radner, F.; Rhodes, C. J. J. Chem. Soc., Perkin Trans. 2 1996, 1289.
31. Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron 1996, 52, 11341.
32. Mizuno, Y.; Simamura, O. J. Chem. Soc. 1958, 3875.
33. Berliner, E.; Powers, J. C. J. Am. Chem. Soc. 1961, 83, 905.
34. Dewar, M. J. S.; Urch, D. S. J. Chem. Soc. 1958, 3079.
35. de la Mare, P. B. D.; Johnson, E. A.; Lomas, J. S. J. Chem. Soc. 1965, 6893.
36. Seshadri, K. V.; Ganesan, R. Tetrahedron 1972, 28, 3827.
37. Kochi, J. K. Angew. Chem. 1988, 100, 1331.
38. Kochi, J. K. Acta Chem. Scand. 1990, 44, 409.
39. Kochi, J. K. Acc. Chem. Res 1992, 25, 39.
40. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1994, 7, 325.
41. Kochi, J. K. Adv. Phys. Org. Chem. 1994, 29, 185.
42. Eberson, L.; Hartshorn, M. P.; Radner, F. Acta Chem. Scand. 1994, 48, 937.
43. Eberson, L.; Hartshorn, M. P.; Radner, F. In Advances in Carbocation Chemistry, Vol. 2; JAI Press Inc.: Greenwich, p 207, 1995.
44. Williamson, S. M. Inorg. Synth. 1968, 11, 147.
45. Fletcher, T. L.; Wetzel, W. H.; Namkung, M. J.; Pan, H.-L J. Am. Chem. Soc. 1959, 81, 1092.
46. Kelm, J.; Strauss, K. Spectrochimica Acta A 1981, 37, 689.
47. Vingiello, F. A.; Quo, S.-G.; Sheridan, J. J. Org. Chem. 1961, 26, 3202.
48. Gascoyne, M. J.; Mitchell, P. J.; Phillips, L. J. Chem. Soc., Perkin Trans. 2 1977, 1051.
49. Nanney, J. R.; Mahaffy, C. A. L. J. Fluorine Chem. 1994, 68, 181.
50. Johnson, R. G.; Willis, H. B.; Martin, G. A.; Kirkpatrick, W. H.; Swiss, J.; Gilman, H. J. Org. Chem. 1956, 21, 457.