Regioselective anodic monofluorination of ethers, lactones, carbonates, and esters using ionic liquid fluoride salts

Journal of the Electrochemical Society

Volumn 153, Issue 10, 2006, Pages

  Hasegawa, Masaru ^a   Ishii, Hideki ^a   Cao, Yi ^a   Fuchigami, Toshio ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b ELECTROCHEMICAL SOCIETY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED ETHERS; FLUORINATION; LACTONES; REGIOSELECTIVITY;

CARBONATES; DISTILLATION; ELECTROLYSIS; ESTERS; ETHERS; REACTION KINETICS;

CATALYST SELECTIVITY;

EID: 33748430355     PISSN: 00134651     EISSN: None     Source Type: Journal    
DOI: 10.1149/1.2222891     Document Type: Article

References (36)

1. Fluorine in Bioorganic Chemistry, J. T. Welch and S. Eswarakrishnan, Editors, Wiley, New York (1991).
2. Organofluorine Compounds, T. Hiyama, Editor, Springer-Verlag, Berlin (2000).
3. T. Fuchigami, in Organic Electrochemistry, 4th ed., H. Lund and O. Hammerich, Editors, Chap. 25, Marcel Dekker, New York (2001).
4. T. Fuchigami, in Advances in Electron-Transfer Chemistry, Vol. 6, P. S. Mariano, Editor, p. 41, JAI Press (1999).
5. T. Tajima, N. Imai, A. Nakajima, H. Kurihara, and T. Fuchigami, J. Electroanal. Chem., 593, 43 (2006).
6. T. Fuchigami, S. Hiashiya, Y. Hou, and K. M. Dawood, Heteroat. Chem., 19, 67 (1999).
7. T. Fuchigami and T. Tajima, in ACS Symposium Series 911. Fluorine-Containing Synthons, V. A. Soloshonok, Editor, Chap. 15, Am. Chem. Soc., Washington, D.C. (2005).
8. G. P. Gambaretto, M. Napoli, C. Franccaro, and L. Conte, J. Fluorine Chem., 19, 427 (1982).
9. J. Meurs and W. Eilenberg, Tetrahedron, 47, 705 (1991).
10. Y. Hou, S. Higashiya, and T. Fuchigami, J. Org. Chem., 64, 3346 (1999).
11. K. M. Dawood and T. Fuchigami, J. Org. Chem., 66, 7691 (2001).
12. M. Hasegawa, H. Ishii, and T. Fuchigami, Green Chem., 5, 512 (2003).
13. K. M. Dawood and T. Fuchigami, J. Org. Chem., 70, 7537 (2005).
14. M. Ue, J. Electrochem. Soc., 141, 3336 (1994).
15. M. Ue, T. Sato, and M. Takeda, Denki Kagaku oyobi Kogyo Butsuri Kagaku, 61, 1080 (1993).
16. R. McMillan, H. Slegr, Z. X. Shu, and W. Wang, J. Power Sources, 81, 20 (1999).
17. R. Mogi, M. Inaba, S. K. Jeong, Y. Iriyama, T. Abe, and Z. Ogumi, J. Electrochem. Soc., 149, A1578 (2002).
18. H. Katayama, J. Arai, and H. Akahoshi, J. Power Sources, 81/82, 705 (1999).
19. M. Inaba, Y. Kawatake, A. Funabiki, S.-K. Jeong, T. Abe, and Z. Ogumi, Electrochim. Acta, 45, 99 (1999).
20. J. L. Adcock and R. J. Lagow, J. Org. Chem., 38, 3617 (1973).
21. M. Kobayashi, T. Inoguchi, T. Iida, T. Tanioka, H. Kumase, S. Yamashita, and Y. Fukai, J. Fluorine Chem., 120, 105 (2003).
22. Y. Sasaki, M. Takehara, S. Watanabe, N. Nanbu, and M. Ue, J. Fluorine Chem., 125, 1205 (2004).
23. Preliminary report: M. Hasegawa, H. Ishii, and T. Fuchigami, Tetrahedron Lett., 43, 1503 (2002).
24. H. Ishii, Y. Hou, and T. Fuchigami, Tetrahedron, 56, 8877 (2000).
25. D. Peters and R. Miethchen, J. Fluorine Chem., 79, 161 (1996).
26. M. Takehara, S. Watanabe, N. Nanbu, M. Ue, and Y. Sasaki, Synth. Commun., 34, 1367 (2004).
27. K. Momota, M. Morita, and Y. Matsuda, Electrochim. Acta, 38, 1123 (1993).
28. S.-Q. Chen, T. Hatakeyama, T. Fukuhara, S. Hara, and N. Yoneda, Electrochim. Acta, 42, 1951 (1997).
29. H. Ishii, N. Yamada, and T. Fuchigami, Chem. Commun. (Cambridge), 2000, 1617 (2000).
30. S. E. Hill, D. Feller, and E. D. Glendening, J. Phys. Chem. A, 102, 3813 (1998).
31. Y. Hou and T. Fuchigami, J. Electrochem. Soc., 147, 4567 (2000).
32. M. R. Shaaban and T. Fuchigami, J. Org. Chem., 65, 8586 (2000).
33. Y. Sasaki, R. Ebara, N. Nanbu, M. Takehara, and M. Ue, J. Fluorine Chem., 108, 117 (2001).
34. T. Shono, Y. Matsumura, K. Inoue, H. Ohmizu, and S. Kashimura, J. Am. Chem. Soc., 104, 5753 (1982).
35. D. Limat, Y. Guggisberg, and M. Schlosser, Liebigs Ann., 5, 849 (1995).
36. S. Watanabe, T. Meguro, N. Nanbu, M. Takehara, M. Ue, and Y. Sasaki, Abstract of 26th Fluorine Conference of Japan, Fukui, Japan, No. R15, p. 116 (2003).