Ionic liquids with fluorine-containing cations

European Journal of Inorganic Chemistry

Volumn , Issue 13, 2005, Pages 2573-2580

  Xue, Hong ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

Cations; Fluorine; Ionic liquids; Quaternization

Indexed keywords

DENSITY OF LIQUIDS; FLUORINE; POSITIVE IONS;

HYDROLYTIC STABILITY; IMIDAZOLIUM; LIQUID RANGE; MORPHOLINIUM; POINT DENSITY; PROPERTY; PYRIDINIUM; PYRROLIDINIUM; QUATERNIZATION; THERMAL;

IONIC LIQUIDS;

EID: 22144494123     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200500129     Document Type: Article

References (60)

1. T. Welton, Chem. Rev. 1999, 99, 2171-2083.
2. P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772-3789.
3. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, Germany, 2003.
4. R. D. Rogers, K. R. Seddon, Ionic Liquids as Green Solvents: Progress and Prospects, ACS Symposium Series 856, American Chemical Society, Washington, DC, 2003.
5. R. D. Rogers, K. R. Seddon, Ionic Liquids: Industrial Applications to Green Chemistry, ACS Symposium Series 818, American Chemical Society, Washington, DC, 2002.
6. R. A. Sheldon, Chem. Commun. 2001, 2399-2407.
7. N. Jain, A. Kumar, S. Chauhan, S. M. S. Chauhan, Tetrahedron 2005, 61, 1015-1060.
8. P. Kubisa, Prog. Polym. Sci. 2004, 29, 3-12.
9. J. H. Davis, Jr., Chem. Lett. 2004, 33(9), 1072-1077.
10. J. H. Davis, Jr.; P. A. Fox, Chem. Commun. 2003, 1209-1212.
11. R. Hagiwara, K. Matsumoto, Y. Nakamori, T. Tsuda, Y. Ito, H. Matsumoto, K. Momota, Proceedings-Electrochemical Society, 2002, 2002-19 (Molten Salts XIII),1007-1013.
12. J. van den Broeke, F. Winter, B. J. Deelman, G. V. Koten, Org. Lett. 2002, 4, 3851-3854.
13. O. D. Gupta, B. Twamley, J. M. Shreeve, Tetrahedron Lett. 2004, 45, 1733-1736.
14. N. V. Ignat'ev, W R. Pitner, Urs Welz-Biermann, M. Weiden, O. Sheppard, C. Hardacre, Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004, ORGN-546.
15. a) Z. B. Zhou, M. Takeda, M. Ue, J. Fluorine Chem. 2004, 125, 471-476;
16. b) Z. B. Zhou, H. Matsumoto, K. Tatsumi, Chem. Eur. J. 2005, 11, 752-766.
17. P. Bonhôte, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, Inorg. Chem. 1996, 35, 1168-1178.
18. T. L. Merrigan, J. H. Davis, Jr., Abstracts of Papers, 220th ACS National Meeting, Washington, DC, United States, August 20-24, 2000, CHED-176.
19. O. D. Gupta, P. D. Armstrong, J. M. Shreeve, Tetrahedron Lett. 2003, 44, 9367-9370.
20. H. Shao, L. Jiang, W. D. Meng, F. L. Qing, J. Fluorine Chem. 2003, 124, 89-91.
21. J. H. Davis, Jr., K. J. Forrester, T. Merrigan, Tetrahedron Lett. 1998, 39, 8955-8958.
22. T. Merrigan, E. D. Bates, S. C. Dorman, J. H. Davis, Jr., Chem. Commun. 2000, 2051-2052.
23. V. R. Koch, C. Nanjundiah, R. T. Carlin, U. S. Patent 5,827,602, 1998. The very broad claims in this patent cover "hydrophobic ionic liquids" with pyridinium, pyridazinium, pyrimidinium, pyrazinium, imidazolium, pyrazolium, thiazolium, oxazolium, and triazolium cores where the rings are frequently substituted with fluorine and/or perfluoro- and polyfluoroalkyl or other fluorine-containing moieties.
24. a) R. P. Singh, S. Manandhar, J. M. Shreeve, Tetrahedron Lett. 2002, 43, 9497-9499;
25. b) R. P. Singh, S. Manandhar, J. M. Shreeve, Synthesis 2003, 10, 1579-1585.
26. C. Ye, J. M. Shreeve, J. Org. Chem. 2004, 69, 6511-6513.
27. K. I. Petko, T. M. Sokolenko, L. M. Yagupolskii, 14th European Symposium on Fluorine Chemistry, Poznan, Poland, July 11-16, 2004, Absract A-O-15.
28. C. M. Jin, J. M. Shreeve, Inorg. Chem. 2004, 43, 7532-7538.
29. B. A. Omotowa, J. M. Shreeve, Organometallics 2004, 23, 783-791.
30. a) Y. R. Mirzaei, B. Twamley, J. M. Shreeve, J. Org. Chem. 2002, 67, 9340-9345;
31. b) Y. R. Mirzaei, J. M. Shreeve, Synthesis 2003, 1, 24-26.
32. H. Xue, B. Twamley, J. M. Shreeve, J. Org. Chem. 2004, 69, 1397-1400.
33. Y. R. Mirzaei, H. Xue, J. M. Shreeve, Inorg. Chem. 2004, 43, 361-367.
34. J. Zhang, G. R. Martin, D. D. DesMarteau, Chem. Commun. 2003, 2334-2335.
35. a) R. P. Singh, J. M. Shreeve, Chem. Commun. 2003, 1366-1367;
36. b) R. P. Singh, J. M. Shreeve, Inorg. Chem. 2003, 42, 7416-7421.
37. Y. Gao, J. M. Shreeve, Synthesis 2004, 7, 1072-1082.
38. R. P. Singh, S. D. Meshri, D. T. Meshri, 14th European Symposium on Fluorine Chemistry, Poznan, Poland, 2004, Abstract C-P-04.
39. R. P. Singh, R. W. Winter, G. L. Gard, Y. Gao, J. M. Shreeve, Inorg. Chem. 2003, 42, 6142-6146.
40. J. Kim, R. P. Singh, J. M. Shreeve, Inorg. Chem. 2004, 43, 2960-2966.
41. a) R. M. Pomaville, C. F. Poole, J. Chromatogr. 1989, 468, 261-278;
42. b) R. M. Pomaville, C. F. Poole, J. Chromatogr. 1990, 468, 749-759.
43. R. Hagiwara, Y. Ito, J. Fluorine Chem. 2000, 105, 221-227.
44. R. Hagiwara, Y. Ito, Electrochemistry (Tokyo) 2002, 70(2), 130-136.
45. P. Waiden, Bull. Acad. Imper. Sci. (St. Petersburg) 1914, 1800.
46. a) J. Sun, M. Forsyth, D. R. MacFarlane, J. Phys. Chem. B 1998, 102, 8858-8864;
47. b) J. Sun, M. Forsyth, D. R. MacFarlane, Molten Salt Forum 1998, 5/6, 585-588;
48. c) A. P. Abbott, G. Capper, D. L. Davies, H. L. Munro, R. K. Rasheed, V. Tambyrajah, Chem. Commun. 2001, 2010-2011;
49. d) H. Matsumoto, M. Yanagida, K. Tanimoto, M. Nomura, Y. Kitagawa, Y. Miyazaki, Chem. Lett. 2000, 922-923;
50. e) B. M. Quinn, A. Ding, R. Moulton, A. J. Bard, Langmuir 2002, 18, 1734-1742;
51. f) Z. B. Zhou, H. Matsumoto, K. Tatsumi, Chem. Lett. 2004, 33(7), 886-887.
52. H. Böhme, M. Hilp, Chem. Ber. 1970, 103, 104-111;
53. H. Niederpruem, P. Voss, V. Beyl, Ger. Offen. DE 1966931, 1975.
54. W. M. Qiu, U. S. Patent 6,054,615, 2000.
55. a) Sagami Chemical Research Center, Japan, Jpn. Kokai Tokkyo Koho, JP 58039664 A2, 1983;
56. b) L. Strekowski, A. S. Kiselyov, Advances in Heterocycl. Chem. 1995, 62, 1-17;
57. c) T. Umemoto, K. Harasawa, G. Tomizawa, K. Kawada, K. Tomita, J. Fluorine Chem. 1991, 53, 369-377;
58. d) C. Rocaboy, F. Hampel, J. A. Gladysz, J. Org. Chem. 2002, 67, 6863-6870;
59. e) S. Alunni, V. Laureti, L. Ottavi, R. Ruzziconi, J. Org. Chem. 2003, 68, 718-725.
60. N. Jain, A. Kumar, S. Chauhan, S. M. S. Chauhan, Tetrahedron 2005, 61, 1015-1060, and references cited therein.