Probing the mechanism of Baylis-Hillman reaction in ionic liquids

Journal of Organic Chemistry

Volumn 77, Issue 19, 2012, Pages 8775-8779

  Singh, Anshu ^a   Kumar, Anil ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

APROTIC POLAR SOLVENTS; BAYLIS-HILLMAN REACTIONS; FIRST ORDER; KINETIC DATA; RATE-DETERMINING STEP; SECOND ORDERS;

ALDEHYDES; ORGANIC COMPOUNDS; ORGANIC SOLVENTS;

IONIC LIQUIDS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACRYLIC ACID; ALDEHYDE; IONIC LIQUID; ORGANIC SOLVENT;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL REACTION KINETICS;

EID: 84867345631     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301348k     Document Type: Article

References (50)

1. Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. Basavaiah, D; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447 and refs. cited therein.
3. Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2007, 48, 4119 and refs. cited therein.
4. Ramachandran, P. V.; Madhi, S.; Bland-Berry, L.; Reddy, M. V. R.; O'Donnell, M. J. J. Am. Chem. Soc. 2005, 127, 13450
5. Trost, B. M.; Machacek, M. R.; Tsui, H. C. J. Am. Chem. Soc. 2005, 127, 7014
6. Kabalka, G. W.; Venkataiah, B.; Dong, G. J. Org. Chem. 2004, 69, 5807
7. Paquette, L. A.; Bennett, G. D.; Isaac, M. B.; Chhatriwalla, A. J. Org. Chem. 1998, 63, 1836
8. Hill, J. S.; Isaacs, N. S. J. Phys. Org. Chem. 1990, 3, 285
9. Bode, M. L.; Kaye, P. T. Tetrahedron Lett. 1991, 32, 5611
10. Robiette, R.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2007, 129, 15513
11. Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2005, 44, 1706
12. Krafft, M. E.; Haxell, T. F. N.; Seibert, K. A.; Abboud, K. A. J. Am. Chem. Soc. 2006, 128, 4174
13. Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135
14. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219
15. Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317
16. Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495
17. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 795
18. Rafel, S.; Leahy, J. W. J. Org. Chem. 1997, 62, 1521
19. Oda, R.; Kawabata, T.; Tanimoto, S. Tetrahedron Lett. 1964, 5, 1653
20. Lee, W.-D.; Yang, K.-S.; Chen, K. Chem. Commun. 2001, 1612
21. Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397
22. Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183 and refs. cited therein.
23. Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510
24. Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147
25. Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980
26. Welton, T. Chem. Rev. 1999, 99, 2071
27. Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391
28. Wasserscheid, P.; Welton, T., Eds. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2003.
29. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667
30. Parvulescu, V. I.; Hardacre, C. Chem. Rev. 2007, 107, 2615
31. Rosa, J. N.; Afonso, C. A. M.; Santos, A. G. Tetrahedron 2001, 57, 4189
32. Johnson, C. L.; Donkor, R. E.; Nawaz, W.; Karodia, N. Tetrahedron Lett. 2004, 45, 7359
33. Afonso, C. A. M.; Branco, L. C.; Candeias, N. R.; Gois, P. M. P.; Lourenco, N. M. T.; Mateus, N. M. M.; Rosa, J. N. Chem. Commun. 2007, 2669
34. Santos, L. S.; Neto, B. A. D.; Consorti, C. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Dupont, J.; Eberlin, M. N. J. Phys. Org. Chem. 2006, 19, 731 and refs. cited therein.
35. Kim, E. J.; Ko, S. Y.; Song, C. E. Helv. Chim. Acta 2003, 86, 894
36. Hsu, J.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. 2004, 45, 4673
37. Zhao, S.-H.; Zhang, H.-R.; Feng, L.-H.; Chen, Z.-B. J. Mol. Catal. A: Chem. 2006, 258, 251
38. Gong, H.; Cai, C-q.; Yang, N-f.; Yang, L-w.; Zhang, J.; Fan, Q-h. J. Mol. Catal. A: Chem. 2006, 249, 236
39. Mi, X.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2005, 70, 2338
40. Tiwari, S.; Kumar, A. Angew. Chem., Int. Ed. 2006, 45, 4824
41. Kumar, A.; Pawar, S. S. J. Mol. Catal. A: Chem. 2004, 211, 43 and refs. cited therein.
42. Tiwari, S.; Khupse, N.; Kumar, A. J. Org. Chem. 2008, 73, 9075
43. Aggarwal, V. K.; Emme, I.; Mereu, A. Chem. Commun. 2002, 1612
44. Chiappe, C.; Pomelli, C. S.; Rajamani, S. J. Phys. Chem. B 2011, 115, 9653
45. Habibi-Yangjeh, A.; Jafari-Tarzanag, Y.; Banaei, A. R. Int. J. Chem. Kinetics 2009, 41, 153
46. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377
47. Himmler, S.; Hormann, S.; Van Hal, R.; Schulz, P. S.; Wasserscheid, P. Green Chem. 2006, 8, 887
48. Kan, H.-C.; Tseng, M.-C.; Chu, Y.-H. Tetrahedron 2007, 63, 1644
49. Anouti, M.; Caillon-Caravanier, M.; Dridi, Y.; Galiano, H.; Lemordant, D. J. Phys. Chem. B 2008, 112, 13335
50. For example see: Stark, A.; Behrend, P.; Braun, O.; Muller, A.; Ranke, J.; Ondruschka, B.; Jastorff, B. Green Chem. 2008, 10, 1152