Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions

Journal of Organic Chemistry

Volumn 70, Issue 11, 2005, Pages 4517-4519

  Ranu, Brindaban C ^a   Banerjee, Subhash ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; IONS; ORGANIC SOLVENTS; REACTION KINETICS; STRUCTURE (COMPOSITION);

HALOHYDRINS; IONIC LIQUIDS; REAGENTS; REGIOSELECTIVE;

ORGANIC COMPOUNDS;

EPOXIDE; NATURAL PRODUCT; REAGENT; SOLVENT;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SELECTIVITY; IONIC STRENGTH; LIQUID; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

CATALYSIS; CHEMISTRY, ORGANIC; EPOXY COMPOUNDS; HYDROCARBONS, HALOGENATED; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 19644382379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500885     Document Type: Article

References (54)

1. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 411.
2. Erickson, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1986; Vol. 5, p 131.
3. Smith, J. G.; Fieser, M. Fieser and Fieser's Reagent for Organic Synthesis; John Wiley and Sons: New York, 1990; Vols 1-12.
4. Stewart, C. A.; Vanderwerf, C. A. J. Am. Chem. Soc. 1954, 76, 1259.
5. Owen, L. N.; Saharia, G. S. J. Chem. Soc. 1953, 2582.
6. (a) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805.
7. (b) Andrews, G. C.; Crawford, T. C.; Contilio, L. G., Jr. Tetrahedron Lett. 1981, 22, 3803.
8. (c) Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249.
9. (d) Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, C. J. Org. Chem. 1987, 52, 1680.
10. Palumbo, G.; Ferreri, C.; Caputo, R. Tetrahedron Lett. 1983, 24, 1307.
11. Weidmann, B.; Seebach, D. Helv. Chim. Acta 1980, 63, 2451.
12. Kagan, J.; Firth, B. E.; Shih, N. Y.; Boyanjian, C. G. J. Org. Chem. 1977, 42, 343.
13. Ciaccio, J. A.; Addess, K. J.; Bell, T. W. Tetrahedron Lett. 1986, 27, 3697.
14. Dave, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061.
15. Einhorn, C.; Luche, J.-L. Chem. Commun. 1986, 1368.
16. Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
17. Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248.
18. Shimizu, M.; Yoshida, A.; Fujisawa, T. Synlett 1992, 204.
19. Yadav, J. S.; Reddy, B. V. S.; Reddy, Ch. S.; Rajasekhar, K. Chem. Lett. 2004, 33, 476.
20. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
21. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3773.
22. (c) Sheldon, R. Chem. Commun. 2001, 2399.
23. (d) Wilkes, J. S. Green Chem. 2002, 4, 73.
24. (a) Yao, Q. Org. Lett. 2002, 4, 2197.
25. (b) Zerth, H. M.; Leonard, N. M.; Mohan, R. S. Org. Lett. 2003, 5, 55.
26. (c) Su, C.; Chen, Z.-C.; Zheng, Q.-G. Synthesis 2003, 555.
27. (d) Rajagopal, R.; Jarikote, D. V.; Lahoti, R. J.; Daniel, T.; Srinivasan, K. V. Tetrahedron Lett. 2003, 44, 1815.
28. (e) Kumar, A.; Pawar, S. S. J. Org. Chem. 2004, 69, 1419.
29. (a) Harjani, J. R.; Nara, S. J.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 1127.
30. (b) Namboodiri, V. V.; Varma, R. S. Chem. Commun. 2002, 342.
31. (c) Sun, W.; Xia, C.-G.; Wang, H.-W. Tetrahedron Lett. 2003, 44, 2409.
32. (d) Qiao, K.; Yakoyama, C. Chem. Lett. 2004, 33, 472.
33. (a) Le, Z -G.; Chen, Z.-C.; Hu, Y.; Zheng, Q.-G. Synthesis 2004, 2809.
34. (b) Earle, M. J.; Katdare, S. P.; Seddon, K. R. Org. Lett. 2004, 6, 707.
35. (a) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 5, 44.
36. (b) Ranu, B. C.; Das, A.; Samanta, S. J. Chem. Soc., Perkin Trans. 1 2002, 1520.
37. (c) Ranu, B. C.; Dey, S. S. Tetrahedron Lett. 2003, 44, 2865.
38. (d) Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2003, 59, 2417.
39. (e) Ranu, B. C.; Dey, S. S. Tetrahedron 2004, 60, 4183.
40. Li, D.; Shi, F.; Peng, J.; Guo, S.; Deng, Y. J. Org. Chem. 2004, 69, 3582.
41. Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212.
42. Rotticci, D.; Rotticci-Mulder, J. C.; Denman, S.; Norin, T.; Hult, K. Chem. Biochem. 2002, 2, 766.
43. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021.
44. Saito, S.; Ishikawa, T.; Kwcoda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067.
45. Federici, C.; Righi, G.; Rossi, L.; Bonini, C.; Funicello, M. Tetrahedron Lett. 1994, 35, 1531.
46. Delmond, B.; Pommier, J.-C. Tetrahedron Lett. 1968, 9, 6147.
47. Zhu, W.; Ford, W. T. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1305.
48. De Buyck, L.; Bostoen, R.; Lecluse, M.; Depooter, H.; Schamp, N. Bull. Soc. Chin. Belg. 1987, 96, 663.
49. Dieter, K. R.; Nice, E. L.; Velu, E. S. Tetrahedron Lett. 1996, 37, 2377.
50. Oliver, S. F.; Hogennauer, K.; Simic, O.; Antonello, A.; Smith, M. D.; Steven, V. Angew. Chem., Int. Ed. 2003, 48, 5996.
51. Molines, H.; Gordon, G.; Waksehman, C. Tetrahedron Lett. 1977, 18, 833.
52. Pouchert, C. J. The Aldrich Library of NMR Spectra, 2nd ed.; Aldrich Chemical Co., Inc.: Milwaukee, 1983; Vols. 1 and 2.
53. Ranu, B. C.; Bhar, S.; Chakraborti, R. J. Org. Chem. 1992, 57, 7349.
54. Sasai, H.; Takeyuki, S.; Shigaru, A.; Takayoshi, A.; Masakatsu, S. J. Am. Chem. Soc. 1992, 114, 4418.