Nucleophilic displacement reactions in ionic liquids: Substrate and solvent effect in the reaction of NaN3 and KCN with alkyl halides and tosylates

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6710-6715

  Chiappe, Cinzia ^a   Pieraccini, Daniela ^a   Saullo, Paola ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DISPLACEMENT REACTIONS;

HALOGEN COMPOUNDS; NEGATIVE IONS; POTASSIUM COMPOUNDS; SODIUM COMPOUNDS; SUBSTRATES;

ORGANIC SOLVENTS;

HALIDE; POTASSIUM CYANIDE; SODIUM DERIVATIVE; SODIUM NITRIDE; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; MOLECULAR DYNAMICS; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 0043011003     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026838h     Document Type: Article

References (53)

1. (a) Holbrey, J. D.; Seddon, K. R Clean Products Processes 1999, 1, 223.
2. (b) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
3. (c) Welton, T. Chem. Rev. 1999, 99, 2071.
4. (d) Wasserscheid, P.; Keim, M Angew. Chem., Int. Ed. 2000, 39, 3773.
5. (e) Sheldon, R. Chem. Commun. 2001, 2399.
6. (e) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182, 419.
7. (f) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
8. Day, S.; Ju, Y. H.; Barnes, C. E. J. Chem. Soc., Dalton Trans. 1999, 1201.
9. Armstrong, D. W.; Zhang, L.-K.; He, L. Gross, M. L. Anal. Chem. 2001, 73, 3679.
10. Dzyuba, S. V.; Barsch, R. A. ChemPhysChem 2002, 3, 161. Huddleston, J. G.; Visser, A. E.; Reichert, W. N.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem, 2001, 3, 156.
11. Dzyuba, S. V.; Barsch, R. A. ChemPhysChem 2002, 3, 161. Huddleston, J. G.; Visser, A. E.; Reichert, W. N.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem, 2001, 3, 156.
12. (a) Grodkowski, J.; Neta, P. J. Phys. Chem. A 2002, 106, 11130.
13. (b) Grodkowski, J.; Neta, P. J. Phys. Chem. A 2002, 106, 5468.
14. (c) McLean, A. J.; Muldoon, M. J.; Gordon, C. M.; Dunkin, I. R. Chem. Commun. 2002, 1880.
15. (d) Owes, G. S.; Abu-Omar, M. M. J. Mol. Catal. A 2002, 3686, 1.
16. Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3 (7), 1061. Chiappe, C.; Conte, V.; Pieraccini, V. Eur. J. Org. Chem. 2002, 2831.
17. Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3 (7), 1061. Chiappe, C.; Conte, V.; Pieraccini, V. Eur. J. Org. Chem. 2002, 2831.
18. Wheeler, C.; West, K. N.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2001, 887. Lancaster, N. L.; Welton, T.; Young, G. B. J. Chem. Soc., Perkin Trans. 2 2001, 2267.
19. Wheeler, C.; West, K. N.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2001, 887. Lancaster, N. L.; Welton, T.; Young, G. B. J. Chem. Soc., Perkin Trans. 2 2001, 2267.
20. Lancaster, N. L.; Saler, P. A.; Welton, T.; Young G. B. J. Org. Chem. 2002, 67, 8855.
21. Judeh, Z. M. A.; Shen, H.-Y. S.; Chi, B. C.; Feng, L.-C.; Selvasothi, S. Tetrahedron Lett. 2002, 9381.
22. (a) Scriven, E. F. V.; Turnbull, K. Chem. Rew. 1988, 88, 298.
23. (b) Stark, C. M. J. Am. Chem. Soc. 1971, 93, 195.
24. (c) Landini, D.; Maia, A.; Montanari, F.; Rolla, F. J. Org. Chem. 1983, 48, 3774.
25. Varma, R. S.; Naicker, K. P. Tetrahedron Lett. 1998, 2915.
26. Lourenqo, N. M. T.; Afonso, C. A. M. Tetrahedron 2003, 59, 789.
27. Anderson, J. L.; Ding, J.; Welton, T.; Armstrong, D. W. J. Am. Chem. Soc. 2002, 124, 14247.
28. (b) Charmichael, A. J.; Seddon, K. R. J. Phys. Org. Chem. 2000, 13, 591.
29. (c) Aki, S. N. V. K.; Brennecke, J. F.; Samanta, A. Chem. Commun. 2001, 413.
30. (d) Muldoon, M. J.; Gordon, C. M.; Dunkin, I. R. J. Chem. Soc., Perkin 2 2001, 433.
31. (e) Fletcher, K. A.; Storey, I. A.; Hendricks, A. E.; Pandey, S.; Pandey, S. Green Chem. 2001, 3, 210.
32. Seddon, K. R.; Stark, A.; Torres, M.-J. Pure Appl. Chem. 2000, 72, 2275.
33. Pearson, R. G. J. Org. Chem. 1987, 52, 2131.
34. Sneen, R. A. Acc. Chem. Res. 1973, 6, 46.
35. Bentley, T. W.; Bowen, C. T.; Morten, D. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 5466 and references therein.
36. Allen, A. D.; Kanagasabapathy, V. M.; Tidwell, T. J. Am. Chem. Soc. 1985, 107, 4513.
37. (a) Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
38. (b) Jencks, W. P. Chem. Soc. Res. 1981, 10, 345.
39. Levene; Rothen; Kuna. J. Biol. Chem. 1937, 120, 789.
40. Nayak, U. G.; Whistler, R. L. J. Org. Chem. 1969, 34, 3819. Hanessian, S.; Vatèle, J.-M. Tetrahedron Lett. 1981, 3579.
41. Nayak, U. G.; Whistler, R. L. J. Org. Chem. 1969, 34, 3819. Hanessian, S.; Vatèle, J.-M. Tetrahedron Lett. 1981, 3579.
42. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1383.
43. Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 2974. Safi, B.; Choho, K.; Geerlings, P. J. Phys. Chem. A 2001, 105, 591.
44. Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 2974. Safi, B.; Choho, K.; Geerlings, P. J. Phys. Chem. A 2001, 105, 591.
45. Pearson, R. G.; Sobel, H.; Songstand, J. J. Am. Chem. Soc. 1968, 90, 319. Ritchie, C. D.; Gandler, J. J. Am. Chem. Soc. 1979, 101, 7318.
46. Pearson, R. G.; Sobel, H.; Songstand, J. J. Am. Chem. Soc. 1968, 90, 319. Ritchie, C. D.; Gandler, J. J. Am. Chem. Soc. 1979, 101, 7318.
47. Mearch, J. Advanced Organic Chemistry: reactions, mechanisms and structure, IVth ed.; J. Wiley & Sons: New York, 1992.
48. Fuller, R. T.; Carlin, H. C.; De Long, D.; Haworth, J. Chem. Soc., Chem. Commun. 1994, 299. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192. Chiappe, C.; Pieraccini, D. Green Chem. 2003, 5, 193.
49. Fuller, R. T.; Carlin, H. C.; De Long, D.; Haworth, J. Chem. Soc., Chem. Commun. 1994, 299. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192. Chiappe, C.; Pieraccini, D. Green Chem. 2003, 5, 193.
50. Fuller, R. T.; Carlin, H. C.; De Long, D.; Haworth, J. Chem. Soc., Chem. Commun. 1994, 299. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192. Chiappe, C.; Pieraccini, D. Green Chem. 2003, 5, 193.
51. Holbrey, J. D.; Seddon, K. R.; Wareing, R. Green Chem. 2001, 3, 33.
52. Billard, I.; Moutiers, G.; El Azzi, A.; Gaillard, C.; Mariet, C.; Lützenkinchen, K. Inorg. Chem. 2003, 42, 1726.
53. Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G. J. Org. Chem. 1980, 45, 299.