New Methods of Free-Radical Perfluoroalkylation of Aromatics and Alkenes. Absolute Rate Constants and Partial Rate Factors for the Homolytic Aromatic Substitution by n-Perfluorobutyl Radical

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7128-7136

  Bravo, Anna ^a   Bjørsvik, Hans René ^a   Fontana, Francesca ^a   Liguori, Lucia ^a   Mele, Andrea ^a   Minisci, Francesco ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001031162     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970302s     Document Type: Article

References (23)

1. Yoshida, M.; Kamigata, N.; Sawada, H.; Nakayama, M. J. Fluorine Chem. 1990, 49, 1 and references therein.
2. Tiers, G. V. D. J. Am. Chem. Soc. 1960, 82, 5513. Cowell, A. B.; Tamborski, C. J. Fluorine Chem, 1981, 17, 345.
3. Tiers, G. V. D. J. Am. Chem. Soc. 1960, 82, 5513. Cowell, A. B.; Tamborski, C. J. Fluorine Chem, 1981, 17, 345.
4. Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am. Chem. Soc. 1977, 99, 7589.
5. Fontana, F.; Minisci, F.; Vismara, E. Free Radicals in Synthesis and Biology; Minisci, F., Ed., Kluwer Acad. Publishers: Dordrecht, 1989; p 53.
6. Brace, N. O. U.S. Pat. 3,271,441 (1966). We thank a referee for this suggestion.
7. (a) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H. Q.; Muir, M. J. Am. Chem. Soc. 1994, 116, 99. J. Org. Chem. 1996, 62, 2027.
8. (a) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H. Q.; Muir, M. J. Am. Chem. Soc. 1994, 116, 99. J. Org. Chem. 1996, 62, 2027.
9. (b) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557.
10. Baciocchi, E.; Muraglia, E. Tetrahedron Lett. 1993, 34, 3799.
11. Minisci, F. Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K. D., Eds.; Plenum Press: New York, 1990; p 303.
12. Bravo, A.; Bjorsvik, H. R.; Fontana, F.; Liguori, L.; Minisci, F. Chem. Commun., 1997, 1501.
13. Minisci, F. Substituent Effects in Free Radical Chemistry; Viehe, H. G., Ed.; Reidel Publishing Co.: Dordrecht, 1986; p 391.
14. Citterio, A.; Arnoldi, A.; Minisci, F. J. Org. Chem. 1979, 44, 2674.
15. Citterio, A.; Minisci, F., Porta, O.; Sesana, G. J. Am. Chem. Soc. 1977, 99, 7960.
16. Shelton, J. R.; Uzelmeier, C. W. J. Am. Chem. Soc. 1966, 88, 5222. Cowley, B. R.; Norman, R. O. C.; Waters, W. A. J. Chem. Soc. 1959, 1799. Corbett, G. E.; Williams, G. H. J. Chem. Soc. 1964, 3437.
17. Shelton, J. R.; Uzelmeier, C. W. J. Am. Chem. Soc. 1966, 88, 5222. Cowley, B. R.; Norman, R. O. C.; Waters, W. A. J. Chem. Soc. 1959, 1799. Corbett, G. E.; Williams, G. H. J. Chem. Soc. 1964, 3437.
18. Shelton, J. R.; Uzelmeier, C. W. J. Am. Chem. Soc. 1966, 88, 5222. Cowley, B. R.; Norman, R. O. C.; Waters, W. A. J. Chem. Soc. 1959, 1799. Corbett, G. E.; Williams, G. H. J. Chem. Soc. 1964, 3437.
19. Minisci, F. Top. Curr. Chem. 1976, 62, 1.
20. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
21. Yoshida, M.; Amemiya, H.; Kobayashi, M.; Sawada, H.; Hagii, H.; Aoshima, K. J. Chem. Soc., Chem. Commun. 1985, 234. Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1989, 46, 423. Kamigata, N.; Ohtsuka, T.; Fukushima, T.; Yoshida, M.; Shimizu, T. J. Chem. Soc., Perkin Trans. 1 1994, 1339.
22. Yoshida, M.; Amemiya, H.; Kobayashi, M.; Sawada, H.; Hagii, H.; Aoshima, K. J. Chem. Soc., Chem. Commun. 1985, 234. Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1989, 46, 423. Kamigata, N.; Ohtsuka, T.; Fukushima, T.; Yoshida, M.; Shimizu, T. J. Chem. Soc., Perkin Trans. 1 1994, 1339.
23. Yoshida, M.; Amemiya, H.; Kobayashi, M.; Sawada, H.; Hagii, H.; Aoshima, K. J. Chem. Soc., Chem. Commun. 1985, 234. Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1989, 46, 423. Kamigata, N.; Ohtsuka, T.; Fukushima, T.; Yoshida, M.; Shimizu, T. J. Chem. Soc., Perkin Trans. 1 1994, 1339.