Synthesis and characterization of organometallic ionic liquids and a heterometallic carbene complex containing the chromium tricarbonyl fragment

Organometallics

Volumn 24, Issue 16, 2005, Pages 4039-4048

  Moret, Marc Etienne ^a   Chaplin, Adrian B ^a   Lawrence, Adrien K ^a   Scopelliti, Rosario ^a   Dyson, Paul J ^a  

^a INSTITUTE OF CHEMICAL SCIENCES AND ENGINEERING   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM COMPOUNDS; COMPLEXATION; IONIC CONDUCTION; MASS SPECTROMETRY; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CARBENE; CHROMIUM TRICARBONYL FRAGMENTS; HETEROMETALLIC COMPLEXES; IONIC LIQUIDS;

SOLUTIONS;

EID: 23844530265     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050283+     Document Type: Article

References (88)

1. (a) Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
2. (b) Welton, T.; Chem. Rev. 1999, 99, 2071.
3. (c) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
4. (a) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H., Jr.; Rogers, R. D. Chem. Commun. 2001, 135.
5. (b) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, R.; Wierzbicki, A.; Davis, J. H., Jr.; Rogers, R. D. Environ. Sci. Technol. 2002, 36, 2523.
6. (c) Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H., Jr. J. Am. Chem. Soc. 2002, 124, 926.
7. Demberelnyamba, D.; Shin, B. K.; Lee, H. Chem. Commun. 2002, 1538.
8. (a) Wang, P.; Zakeeruddin, S. M.; Exnar, I.; Gratzel, M. Chem. Comun. 2002, 2972.
9. (b) Wang, P.; Zakeeruddin, S. M.; Comte, P.; Exnar, I.; Gratzel, M. J. Am. Chem. Soc. 2003, 125, 1166.
10. (a) Liu, W. M.; Chen, Y. X.; Yu, L. G. Chem. Comun. 2001, 2244.
11. (b) Li, W. M.; Ye, C. F.; Gong, Q. Y.; Wang, H. Z.; Wang, P. Tribology Lett. 2002, 13, 81.
12. (a) Armstrong, D. W.; Zhang, L. K.; He, L. F.; Gross, M. L. Anal. Chem. 2001, 73, 3679.
13. (b) Carda-Broch, S.; Berthod, A.; Armstrong, D. W. Rapid Commun. Mass Spectrom. 2003, 17, 553.
14. Gamero-Castano, M.; Hruby, V.; Propuls J. Power 2001, 17, 977.
15. Herrmann, W. A.; Köcher, C.; Goossen, L. J.; Artus, G. R. J. Chem.-Eur. J. 1996, 2, 1627.
16. Lee, K.-M.; Lee, Y.-T.-Y.; Lin, J. B. J. Mater. Chem. 2003, 13, 1079.
17. (a) Zhao, D.; Fei, Z.; Scopelliti R.; Dyson, P. J. Inorg. Chem. 2004, 43, 2197.
18. (b) Zhao, D.; Fei, Z.; Geldbach, T. J.; Scopelliti R.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 15876.
19. Branco, L. C.; Rosa, J. N.; Moura Ramos, J. J.; Alfons, C. A. M. Chem.-Eur. J. 2002, 8, 3671.
20. (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H., Jr. J. Am. Chem. Soc. 2002, 124, 5962.
21. (b) Holbrey, J. D.; Reichert, W. M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi, I. Chem. Commun. 2003, 28.
22. Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H., Jr.; Rogers, R. D. Chem. Commun. 2001, 135.
23. Merrigan, T. L.; Bates, E. D.; Dorman, S. C.; Davis, J. H., Jr. Chem. Commun. 2000, 2051.
24. (a) Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23.
25. (b) Wasserscheid, P.; Bösmann, A.; Bolm, C. Chem. Commun. 2002, 200.
26. (c) Bicak, N. J. Mol. Liquids 2005, 116, 15.
27. (a) Yoshizawa, M.; Ogihara, W.; Ohno, H. Polym. Adv. Technol. 2002, 13, 589.
28. (b) Ohno, H.; Yoshizawa, M.; Ogihara, W. Electrochim. Acta 2004, 50, 255.
29. (a) Ogihara, W.; Yoshizawa, M.; Ohno, H. Chem. Lett. 2004, 33, 1022.
30. (b) Xue, H.; Gao, Y.; Twamley, B.; Shreeve, J. M. Chem. Mater. 2005, 17, 191.
31. (c) Katritzky, A. R.; Singh, S.; Kirichenko, K.; Holbrey, J. D.; Smiglak, M.; Reichert, W. M.; Rogers, R. D. Chem. Commun. 2005, 868.
32. Kim, H. S.; Kim, Y. J.; Lee, H.; Park, K. Y.; Lee, C.; Chin, C. S. Angew. Chem., Int. Ed. 2002, 41, 4300.
33. (a) Zhao, D.; Fei, Z.; Ohlin, C. A.; Laurenczy, G.; Dyson, P. J. Chem. Commun. 2004, 2500.
34. (b) Fei, Z.; Zhao, D.; Geldbach, T. J.; Scopelitti, R.; Dyson, P. J. Eur. J. Inorg. Chem. 2005, 860.
35. (c) Matsumoto, H.; Tatsumi, K. Chem.-Eur. J. 2005, 10, 6581.
36. (d) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Chem.-Eur. J. 2005, 11, 752.
37. Larsen, A. S.; Holbrey, J. D.; Tham, F. S.; Reed, C. A. J. Am. Chem. Soc. 2000, 122, 7264.
38. Dyson, P. J. Appl. Organomet. Chem. 2002, 16, 495.
39. Chauvin, Y.; Gilbert, B.; Guibard, I. J. Chem. Soc., Chem. Commun. 1990, 1715.
40. Carlin, R. T.; Osteryoung, R. A. J. Mol. Catal. 1990, 63, 125.
41. Brown, R. J. C.; Dyson, P. J.; Ellis, D. J.; Welton, T. Chem. Commun. 2001, 1862.
42. Dyson, P. J.; Mclndoe, J. S.; Zhao, D. Chem. Commun. 2003, 508.
43. Gao, Y.; Twamley, B.; Shreeve, J. M. Inorg. Chem 2004, 43, 3406.
44. (a) Schottenberger, H.; Wurst, K.; Horvath, U. E. I.; Cronje, S.; Lukasser, J.; Polin, J.; McKenzie, J. M.; Raubenheimer, H. G. J. Chem. Soc., Dalton Trans. 2003, 4257.
45. (b) Fei, Z.; Zhao, D.; Scopelliti, R.; Dyson, P. J. Organometallics 2004, 23, 1622.
46. (a) Dyson, P. J.; Humphrey, D. G.; McGrady, J. E.; Mingos, D. M.; Wilson, D. J. J. Chem. Soc., Dalton Trans. 1995, 4039.
47. (b) Uemura, M. Adv. Met. Org. Chem. 1991, 2, 195.
48. (c) Strohmeier, W. Chem. Ber. 1961, 94, 2490.
49. Christofi, A. M.; Garratt, P. J.; Hogarth, G.; Steed, J. W. J. Chem. Soc., Dalton Trans. 2000, 2137.
50. Gibson, S. E.; Schmid, G. A. Chem. Commun. 1997, 865.
51. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA.: 2002.
52. Dyson, P. J.; Mclndoe, J. S. Inorg. Chim. Acta 2003, 354, 68.
53. For examples, see ref 29 and: (a) Mahaffy C. A. L.; Pauson, P. L. Inorg. Synth. 1979, 19, 154.
54. (b) Hunter, A. D.; Mozol, V.; Tsal, S. D. Organometallics 1992, 11, 2251.
55. Morris, M. J. In Comphrehensive Organometallic Chemistry II; Abel, E. W., Stone, P. G. A., Eds.; Wilkinson, G. Pergainon Press: Oxford, 1995; Vol. 5, pp 471-549.
56. (a) Lee, H. M.; Lu, C. Y.; Chen, C. Y.; Chen, W. L.; Lun, H. C.; Chiu, P. L.; Cheng, P. Y. Tetrahedron 2004, 60, 5807.
57. (b) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132.
58. (c) Grobosch, T.; Sawusch, S.; Schilde, U.; Uhlemann, E. Z. Kristallogr. New Cryst. Struct. 1998, 213, 173.
59. (d) Elaiwi, A.; Hitchcock, P. B.; Seddon, K. R.; Srinivasan, N.; Tan, Y.-M.; Welton, T.; Zora, J. A. J. Chem. Soc., Dalton Trans. 1995, 3467.
60. Yoshida, Y.; Sakakura, Y.; Aso, N.; Okada, S.; Tanabe, Y. Tetrahedron 1999, 55, 2183.
61. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
62. For recent reviews, see (a) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
63. (b) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
64. (a) Braun, W.; Salzer, A.; Spindler, F.; Alberico, E. Appl.Catal., A 2004, 274, 191-203.
65. (b) Salzer, A. Coord. Chem. Rev. 2003, 242, 59-72.
66. (c) Bolm C.; Muñiz, K. Chem. Soc. Rev. 1999, 28, 51.
67. (a) Lin, I. J. B.; Vasam, C. S. Comments Inorg. Chem. 2004, 25, 75-129.
68. (b) Csabai P.; Joó, F. Organometallics 2004, 23, 5640 and references therein.
69. (a) Ozdemir, I.; Yigit, B.; Cetinkaya, B.; Vlku, D.; Tahir, M. N.; Arici, C. J. Organomet. Chem. 2001, 633, 27.
70. (b) Cetinkaya, B.; Demir, S.; Ozdemir, I.; Toupet, L.; Semeril, D.; Bruneau, C.; Dixneuf, P. H. Chem - Eur. J. 2003, 9, 2323.
71. (c) Cetinkaya, B.; Demir, S.; Ozdemir, I.; Toupet, L.; Semeril, D.; Bruneau, C.; Dixneuf, P. H. Nouv. J. Chim. 2001, 25, 519.
72. (d) Arslan, H.; Vanderveer, D.; Ozdemir, I.; Cetinkaya, B.; Yasar, S. Z. Kristallogr. New Cryst. Struct. 2004, 219, 44.
73. 3at -50°C of the upfield diastereotopic H3″ (173 Hz) and H6″ (140 Hz) resonances are significantly smaller than those of the corresponding downfield resonances H3′ (176 Hz) and H6′ (144 Hz), consistent with the presence of hydrogen bonding in solution.
74. Dyson, P. J.; Grossel, M. C.; Srinivasan, N.| Vine, T.; Welton, T.; Williams, D. J.; White, A. J.; Zigras, T. J. Chem. Soc., Dalton Trans. 1997, 3465.
75. Stark A.; MacLean, B. L.; Singer, R. D. J. Chem. Soc., Dalton Trans. 1999, 63.
76. Crofts, D.; Dyson, P. J.; Sanderson, K. M.; Srinivasan, N.; Welton, T. J. Organomet. Chem. 1999, 573, 292.
77. Husan, M.; Kozhevnikov, I. V.; Siddiqui, M. R. H.; Steiner, A.; Winterton, N. J. Chem. Res. (S) 2000, 392.
78. Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123.
79. Gao, G.; Xiao, R.; Yuan, Y.; Zhou, C.-H.; You, J.; Xie, R.-G. J. Chem. Res. (S) 2002, 6, 262.
80. Ohlin, C. A. Ph.D. Thesis, Ecole Polytechnique Fédérale de Lausanne, 2004.
81. Kasuga, K.; Kato, T.; Kabata N.; Handa M. Bull. Chem. Soc. Jpn. 1996 69, 2885.
82. Bennett, M. A.; Huang, T. N.; Matheson, T. W.; Smith, A. K. Inorg. Synth. 1982, 21, 74.
83. Vidiš, A.; Ohlin, C. A.; Laurenczy, G.; Küsters, E.; Sedelmeier, G.; Dyson, P. J. Adv. Synth. Catal. 2005, 347, 266.
84. Oxford Diffraction Ltd., Abingdon, Oxfordshire, U.K., 2003.
85. Sheldrick, G. M. SHELXTL; University of Göttingen: Germany, 1997; Bruker AXS, Inc.: Madison, WI, 1997.
86. Altomare, A.; Burla, M. G.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
87. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A 1983, 39, 158.
88. Diamond 3.0a; Crystal Impact GbR, Bonn, Germany, 2004.