Application of Ionic Liquid Halide Nucleophilicity for the Cleavage of Ethers: A Green Protocol for the Regeneration of Phenols from Ethers

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3340-3344

  Boovanahalli, Shanthaveerappa K ^a   Kim, Dong Wook ^a   Chi, Dae Yoon ^a  

^a Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; NAPHTHALENE; PHENOLS; SULFUR COMPOUNDS;

DEALKYLATION; DEMETHYLATION; NUCLEOPHILICITY;

ETHERS;

1 N BUTYL 3 METHYLIMIDAZOLIUM BROMIDE; BROMIDE; ETHER DERIVATIVE; HALIDE; NAPHTHALENE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIQUID; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 2442574811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035886e     Document Type: Article

References (41)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; pp 246-276.
2. For reviews on cleavage of ethers, see: (a) Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249-282.
3. (b) Tiecco, M. Synthesis 1988, 749-759.
4. (c) Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972-989.
5. (d) Ranu, B. C.; Bhar, S. Org. Prep. Proced. Int. 1996, 28, 371-409.
6. (a) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH (UK), Ltd.: Cambridge, UK, 1998.
7. (b) Martin, D.; Weise, A.; Niclas, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 318-334.
8. (c) Normant, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 1046-1067.
9. (d) Parker, A. J. Chem. Rev. 1969, 69, 1-32.
10. (e) Sowinski, A. F.; Whitesides, G. M. J. Org. Chem. 1979, 44, 2369-2376.
11. (f) Hutchins, R. O.; Taffer, I. M. J. Org. Chem. 1983, 48, 1360-1362.
12. (a) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278-10279.
13. (b) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285.
14. (c) Kim, D. W.; Choe, Y. S.; Chi, D. Y. Nucl. Med. Biol. 2003, 30, 345-350.
15. (a) Wheeler, C.; West, K. N.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2001, 887-888.
16. (b) Badri, M.; Brunet, J.-J. Tetrahedron Lett. 1992, 33, 4435-4438.
17. (c) Judeh, Z. M. A.; Shen, H.-Y.; Chi, B. C.; Feng, L.-C.; Selvasothi, S. Tetrahedron Lett. 2002, 43, 9381-9384.
18. (d) Chiappe, C.; Pieraccini, D.; Saullo, P. J. Org. Chem. 2003, 68, 6710-6715.
19. (e) Lourenco, N. M. T.; Afonso, C. A. M. Tetrahedron 2003, 59, 789-794.
20. For recent reviews on ionic liquids, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407.
21. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
22. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
23. (d) Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A.-C.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2003, 14, 3081-3093.
24. (e) Rogers, R. D.; Seddon, K. R. Science 2003, 302, 792-793.
25. Ford, W. T.; Hauri, R. J.; Smith, S. G. J. Am. Chem. Soc. 1974, 96, 4316-4318.
26. (a) Brauman, J. I.; Olmstead, W. N.; Lieder, C. A. J. Am. Chem. Soc. 1974, 96, 4030-4031.
27. (b) Olmstead, W. N.; 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) Lancaster, N. L.; Welton, T.; Young, G. B. J. Chem. Soc., Perkin Trans. 2 2001, 2267-2270.
30. (b) Lancaster, N. L.; Salter, P. A.; Welton, T.; Young, G. B. J. Org. Chem. 2002, 67, 8855-8861.
31. (a) Avent, A. G.; Chaloner, P. A.; Day, M. P.; Seddon, K. R.; Welton, T. J. Chem. Soc., Dalton Trans. 1994, 3405-3413.
32. (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.
33. (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.
34. Cannizzaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
35. (a) Sethi, A. R.; Welton, T. In Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002; pp 241-246.
36. (b) Aggarwal, A.; Lancaster, N. L.; Sethi, A. R.; Welton, T. Green Chem. 2002, 4, 517-520.
37. Dzyuba, S. V.; Bartsch, R. A. Tetrahedron Lett. 2002, 43, 4657-4659.
38. Kemperman, G. J.; Roeters, T. A.; Hilberink, P. W. Eur. J. Org. Chem. 2003, 1681-1686.
39. Green, L.; Hemeon, I.; Singer, R. D. Tetrahedron Lett. 2000, 41, 1343-1346.
40. Driver, G.; Johnson, K. E. Green Chem. 2003, 5, 163-169.
41. Moderate isolated yield can be attributed to the poor solubility of 7-hydroxycoumarin in ether at room temperature; hence, product was isolated with warm ether.