An in-depth look at the effect of Lewis acid catalysts on Diels-Alder cycloadditions in ionic liquids

Tetrahedron

Volumn 61, Issue 30, 2005, Pages 7105-7111

  Silvero, Guadalupe ^a   Arévalo, María José ^a   Bravo, José Luis ^a   Ávalos, Martín ^a   Jiménez, José Luis ^a   López, Ignacio ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

Diels Alder cycloaddition; Ionic liquids; Lewis acid

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; LEWIS ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ION PERMEABILITY; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

BETULACEAE;

EID: 20544470946     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.064     Document Type: Article

References (52)

1. F. Fringuelli, and A. Taticchi The Diels-Alder Reaction Selected Practical Methods 2002 Wiley Chichester
2. P. Areces, M. Ávalos, R. Babiano, P. Cintas, L. González, M.B. Hursthouse, J.L. Jiménez, M.E. Light, I. López, J.C. Palacios, and G. Silvero Eur. J. Org. 2001 2135
3. M.J. Arévalo, M. Ávalos, R. Babiano, P. Cintas, M.B. Hursthouse, J.L. Jiménez, M.E. Light, I. López, and J.C. Palacios Tetrahedron Lett. 40 1999 8675
4. M. Ávalos, R. Babiano, P. Cintas, M.B. Hursthouse, J.L. Jiménez, M.E. Light, I. López, and J.C. Palacios Chem. Commun. 1999 1589
5. M. Ávalos, R. Babiano, P. Cintas, M.B. Hursthouse, J.L. Jiménez, M.E. Light, I. López, J.C. Palacios, and G. Silvero Chem. Eur. J. 7 2001 3033
6. M.J. Arévalo, M. Ávalos, R. Babiano, P. Cintas, M.B. Hursthouse, J.L. Jiménez, M.E. Light, I. López, and J.C. Palacios Tetrahedron 56 2000 1247
7. M.J. Arévalo, M. Ávalos, R. Babiano, P. Cintas, M.B. Hursthouse, J.L. Jiménez, M.E. Light, and J.C. Palacios Tetrahedron: Asymmetry 13 2002 223
8. M. Ávalos, R. Babiano, J.L. Bravo, P. Cintas, J.L. Jiménez, and J.C. Palacios Tetrahedron Lett. 39 1998 9301
9. M. Ávalos, R. Babiano, J.L. Bravo, P. Cintas, J.L. Jiménez, J.C. Palacios, and M.A. Silva Green Chem. 3 2001 26
10. M. Ávalos, R. Babiano, J.L. Bravo, P. Cintas, J.L. Jiménez, J.C. Palacios, and B.C. Ranu Tetrahedron Lett. 39 1998 2013
11. H. Zhao, and S.V. Malhotra Aldrichim. Acta 35 2002 75
12. H. Olivier-Bourbigou, and L. Magna J. Mol. Catal. A: Chem. 419 2002 182 183
13. D. Zhao, M. Wu, Y. Kou, and E. Min Catal. Today 74 2002 157
14. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667
15. C.M. Gordon Appl. Catal. A 222 2001 101
16. J.F. Brennecke, and E.J. Maginn AIChE J. 47 2001 2384
17. R. Sheldon Chem. Commun. 2001 2399
18. P. Wasserscheid T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
19. J. Dupont, and J. Spencer Angew. Chem., Int. Ed. 43 2004 5296
20. R.P. Swatkoski, J.D. Holbrey, and R.D. Rogers Green Chem. 5 2003 361
21. J.D. Oxley, T. Prozorov, and K.S. Suslick J. Am. Chem. Soc. 125 2003 11138
22. U. Kumar Sur, F. Marken, B.A. Coles, R.G. Compton, and J. Dupont Chem. Commun. 2004 2816
23. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. Engl. 39 2000 3772
24. P. Wasserscheid, R. van Hal, and A. Bösmann Green Chem. 4 2002 400
25. D.A. Jaeger, and C.E. Tucker Tetrahedron Lett. 30 1989 1785
26. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097
27. C.W. Lee Tetrahedron Lett. 40 1999 2461
28. T. Fischer, A. Sethi, T. Welton, and J. Woolf Tetrahedron Lett. 40 1999 793
29. M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 1 1999 23
30. C.E. Song, W.H. Shim, E.J. Roh, S. Lee, and J.H. Choi Chem. Commun. 2001 1122
31. P. Ludley, and N. Karodia Tetrahedron Lett. 42 2001 2011
32. A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, and V. Tambyrajah Green Chem. 4 2002 24
33. I. Meracz, and T. Oh Tetrahedron Lett. 44 2003 6465
34. Y. Xiao, and S.V. Malhotra Tetrahedron Lett. 45 2004 8339
35. S. Doherty, P. Goodrich, C. Hardacre, H.-K. Luo, D.W. Rooney, K.R. Seddon, and P. Styring Green Chem. 6 2004 63
36. C.W. Lee Tetrahedron Lett. 40 1999 2461
37. A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, and V. Tambyrajah Green Chem. 4 2002 24
38. 2O was determined to be 5≤n≤6 by Laali et al. K.K. Laali, M. Herbert, B. Cushnyr, A. Bhatt, and D. Terrano J. Chem. Soc., Perkin Trans. 1 2001 578
39. V. Branchadell, A. Oliva, and J. Bertran J. Mol. Struct. (Theochem) 138 1986 117
40. N.D. Epiotis, and S. Shaik J. Am. Chem. Soc. 100 1978 1
41. S. Kobayashi, I. Hachiya, T. Takahori, M. Araki, and H. Ishitani Tetrahedron Lett. 33 1992 6815
42. A. Keshevaraja, V.R. Hegde, B. Pandey, A.V. Ramaswamy, P. Kumar, and T. Rabindranathan Angew. Chem., Int. Ed. Engl. 34 1995 2143
43. S. Kobayashi Synlett 1994 689
44. S. Kobayashi, I. Hachiya, M. Araki, and H. Ishitani Tetrahedron Lett. 34 1993 3755
45. T.-P. Loh, J. Pei, and M. Lin Chem. Commun. 1996 2315
46. Corrigendum: (b) Chem. Commun. 1996 2315
47. Z. Zhu, and J.H. Espenson J. Am. Chem. Soc. 119 1997 3507
48. S. Kobayashi, T. Tsuchiya, I. Komoto, and J. Matsuo J. Organomet. Chem. 624 2001 392
49. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923
50. C. Villagrán, M. Deetlefs, W.R. Pitner, and C. Hardacre Anal. Chem. 76 2004 2118
51. This synthesis was accomplished by a method adapted from the general procedure described in Ref. 6h (pp 7-19).
52. J. Mendam, R.C. Dennery, J.D. Barnes, and M. Thomas Vogel's Textbook of Quantitative Chemical Analysis 6th ed. 2000 Prentice Hall Harlow