Significantly enhanced reactivities of the nucleophilic substitution reactions in ionic liquid

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4281-4285

  Kim, Dong Wook ^a   Song, Choong Eui ^b   Chi, Dae Yoon ^a  

^a Inha University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL COMPOUNDS; FLUORIDE MINERALS; HALOGENATION; SUBSTITUTION REACTIONS;

NUCLEOPHILIC SUBSTITUTION;

ORGANIC COMPOUNDS;

1 N BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 2 (3 ACETOXYPROPYL)NAPHTHALENE; 2 (3 BROMOPROPYL)NAPHTHALENE; 2 (3 CYANOPROPYL)NAPHTHALENE; 2 (3 FLUOROPROPYL)NAPHTHALENE; 2 (3 METHANESULFONYLOXYPROPYL)NAPHTHALENE; 2 (3 METHOXYPROPYL)NAPHTHALENE; ACETIC ACID; ALKANE DERIVATIVE; BORIC ACID; CYANIDE; FLUORIDE; FLUORINE DERIVATIVE; IMIDAZOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; POTASSIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; FLUORINATION; HALOGENATION; IONIZATION; LIQUID; REACTION ANALYSIS;

EID: 0038441555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034109b     Document Type: Article

References (43)

1. Smith, M. D.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley-Interscience: New York, 2001; pp 389-674.
2. (a) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH (UK) Ltd.: Cambridge, U.K., 1998.
3. (b) Martin, D.; Weise, A.; Niclas, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 318-334.
4. (c) Normant, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 1046-1067.
5. (d) Parker, A. J. Chem. Rev. 1969, 69, 1-32.
6. (e) Sowinski, A. F.; Whitesides, G. M. J. Org. Chem. 1979, 44, 2369-2376.
7. (f) Hutchins, R. O.; Taffer, I. M. J. Org. Chem. 1983, 48, 1360-1362.
8. (a) Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: Cambridge, 1991.
9. (b) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036.
10. (c) Liotta, C. L.; Harris, H. P. J. Am. Chem. Soc. 1974, 96, 2250-2252.
11. (d) Sam, D. J.; Simmons, H. E. J. Am. Chem. Soc. 1974, 96, 2252-2253.
12. (a) Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed.; VCH Ltd.: New York, 1993.
13. (b) Dehmlow, E. V. Angew. Chem., Int. Ed. Engl. 1977, 16, 493-505.
14. (c) Starks, C. M. J. Am. Chem. Soc. 1971, 93, 195-199.
15. (d) Starks, C. M.; Owens, R. M. J. Am. Chem. Soc. 1973, 95, 3613-3617.
16. (a) Regen, S. L.; Lee, D. P. J. Am. Chem. Soc. 1974, 96, 294-296.
17. (b) Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956-5957; J. Am. Chem. Soc. 1976, 98, 6270-6274; J. Org. Chem. 1977, 42, 875-879.
18. (b) Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956-5957; J. Am. Chem. Soc. 1976, 98, 6270-6274; J. Org. Chem. 1977, 42, 875-879.
19. (b) Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956-5957; J. Am. Chem. Soc. 1976, 98, 6270-6274; J. Org. Chem. 1977, 42, 875-879.
20. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278-10279.
21. 2], and acetate [OAc]-are used.
22. For reviews on nucleophilic fluorination, see: (a) Gerstenberger, M. R. C.; Haas, A. Angew. Chem., Int. Ed. Engl. 1981, 20, 647-667.
23. (b) Mascaretti, O. A. Aldrichim. Acta 1993, 26, 47-58.
24. (a) Colonna, S.; Re, A.; Gelbard, G.; Cesarotti, E. J. Chem. Soc., Perkin Trans. 1 1979, 2248-2252.
25. (b) Ishikawa, N.; Kitazume, T.; Yamazaki, T.; Mochida, Y.; Tatsumo, T. Chem. Lett. 1981, 761-764.
26. (c) Clark, J. H.; Hyde, A. J.; Smith, D. K. J. Chem. Soc., Chem. Commun. 1986, 791-793.
27. (d) Ichihara, J.; Matsuo, T.; Hanafusa, T.; Ando, T. J. Chem. Soc., Chem. Commun. 1986, 793-794.
28. (e) Cox, D. P.; Terpinsky, J.; Lawrynowicz, W. J. Org. Chem. 1984, 49, 3216-3219.
29. (f) Chi, D. Y.; Kilbourn, M. R.; Katzenellenbogen, J. A.; Welch, M. J. J. Org. Chem. 1987, 52, 658-664.
30. (g) Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167.
31. (h) Garayt, M.; Le Boulaire, V.; Gree, D.; Gree, R.; Schanen, V.; Spindler, J.-F. PCT Int. Appl. PIXXD2 WO 0292608, 2002, 59 pp.
32. For recent reviews on ionic liquids, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
33. For recent reviews on ionic liquids, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
34. For recent reviews on ionic liquids, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
35. (a) Song, C. E.; Shim, W. H.; Roh, E. J.; Lee, S.-g.; Choi, J. H. Chem. Commun. 2001, 1122-1123.
36. (b) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695-1696.
37. (c) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838.
38. (a) Lancaster, N. L.; Welton, T.; Young, G. B. J. Chem. Soc., Perkin Trans. 2 2001, 2267-2270.
39. (b) Lancaster, N. L.; Salter, P. A.; Welton, T.; Young, G. B. J. Org. Chem. 2002, 67, 8855-8861.
40. Wheeler, C.; West, K. N.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2001, 887-888.
41. Lourenco, N. M. T.; Afonso, C. A. M. Tetrahedron 2003, 59, 789-794.
42. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977-979.
43. Dijkstra, G.; Kruizinga, W. H.; Kellog, R. H. J. Org. Chem. 1987, 52, 4230-4234.