Nucleophilicity in ionic liquids. 2.1 Cation effects on halide nucleophilicity in a series of bis(trifluoromethylsulfonyl)imide ionic liquids

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 8855-8861

  Llewellyn Lancaster, N ^a   Salter, Paul A ^a   Welton, Tom ^a   Brent Young, G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUIDS; NUCLEOPHILICITY;

BROMINE COMPOUNDS; CHLORINE COMPOUNDS; IODINE COMPOUNDS; POSITIVE IONS;

ORGANIC COMPOUNDS;

BIS(TRIFLUOROMETHYLSULFONYL)IMIDE; BROMIDE; CHLORIDE; DICHLOROMETHANE; HALIDE; IMIDAZOLE DERIVATIVE; IMIDE; IODIDE; ION; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; LIQUID; MOLECULAR INTERACTION; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY;

EID: 0037073935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026113d     Document Type: Article

References (38)

1. Part 1: see ref 5.
2. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
3. (b) Wassercheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
4. (c) Sheldon, R. Chem. Commun. 2001, 2399-2407.
5. (d) Gordon, C. M. Appl. Catal., A 2001, 222, 101-117.
6. (e) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182, 419-437.
7. (f) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157-189.
8. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd Ed.; VCH (UK) Ltd.: Cambridge, U.K., 1998.
9. Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; VCH Wiley: Weinheim, Germany, 2002; see also references therein.
10. Lancaster, N. L.; Welton, T.; Young, G. B. J. Chem. Soc., Perkin Trans. 2 2001, 2267-2270.
11. Ford, W. T.; Hauri, R. J.; Smith, S. G. J. Am. Chem. Soc. 1974, 96, 4316-4318.
12. Wheeler, C.; West, K. N.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2001, 887-888.
13. Alluni, S.; Pero, A.; Reichenbach, G. J. Chem. Soc., Perkin Trans. 2 1998, 1747-1750.
14. Alluni, S.; Pica, M.; Reichenbach, G. J. Phys. Org. Chem. 2001, 14, 265-270.
15. Bunting, J. W.; Mason, J. M.; Heo, C. K. M. J. Chem. Soc., Perkin Trans. 2 1994, 2291-2300.
16. Kurz, J. L.; Lu, J. Y.-W. J. Phys. Chem. 1983, 87, 1444-1448.
17. Dietze, P. E.; Hariri, R.; Khattak, J. J. Org. Chem. 1989, 54, 3317-3320.
18. Reference 3, Table 5-15, p 215 and references therein.
19. Okoturo, O. O.; Pell, T.; VanderNoot, T. J. Private communication.
20. Lancaster, N. L.; Welton, T.; Young, G. B. Unpublished data.
21. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd Ed.; Bell: London, 1969.
22. (a) Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1935, 244-255.
23. (b) Hughes, E. D. Trans. Faraday Soc. 1941, 37, 603-632.
24. (c) Hughes, E. D.; Ingold, C. K. Trans. Faraday Soc. 1941, 37, 657-686.
25. (d) Cooper, K. A.; Dhar, M. L.; Hughes, E. D.; Ingold, C. K.; MacNulty, B. J.; Woolf, L. I. J. Chem. Soc. 1948, 2043-2049.
26. (a) Brauman, J. I.; Olmstead, W. N.; Lieder, C. A. J. Am. Chem. Soc. 1974, 96, 4030-4031.
27. (b) Lieder, C. A.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 4219-4228.
28. (c) Tanaka, K.; Mackay, G. I.; Payzant, J. D.; Bohme, D. K. Can. J. Chem. 1976, 54, 1643-1659.
29. (a) Avent, A. G.; Chaloner, P. A.; Day, M. P.; Seddon, K. R.; Welton, T. J. Chem. Soc., Dalton Trans. 1994, 3405-3413.
30. (b) Abdul-Sada, A. K.; Al-Juaid, S.; Greenway, A. M.; Hitchcock, P. B.; Howells, M. J.; Seddon, K. R.; Welton, T. Struct. Chem. 1990, 1, 391-394.
31. (c) Elaiwi, A.; Hitchcock, P. B.; Seddon, K. R.; Srinivasan, N.; Tan, Y.-M.; Welton, T.; Zora, J. A. J. Chem. Soc., Dalton Trans. 1995, 3467-3472.
32. Cannizzaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
33. (a) Sethi, A. R.; Welton, T. In Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series No. 818; American Chemical Society, Washington, DC, 2002; pp 241-246.
34. (b) Aggarwal, A.; Lancaster, N. L.; Sethi, A. R.; Welton, T. Green Chem. 2002, 4, 517-520.
35. Dzyuba, S. V.; Bartsch, R. A. Tetrahedron Lett. 2002, 43, 4657- 4659.
36. Hardacre, C.; Holbrey, J. D.; McMath, S. E. J.; Bowron, D. T.; Sopev, A. K. In Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series No. 818; American Chemical Society: Washington, DC, 2002; pp 400-412.
37. See, for example: Freemantle, M. Chem. Eng. News 1998, 76 (34, Aug 24), 12.
38. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.