Synthetic and theoretical study on proline-catalyzed Knoevenagel condensation in ionic liquid

Journal of Molecular Catalysis A: Chemical

Volumn 253, Issue 1-2, 2006, Pages 212-221

  Wang, Yun ^a   Shang, Zhi cai ^a   Wu, Tian xing ^a   Fan, Ji cai ^a   Chen, Xiang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Gaussian 98; Ionic liquid; l proline; Solvation energies; The Knoevenagel condensation

Indexed keywords

ALDEHYDES; CATALYSIS; CONDENSATION; IONIC CONDUCTION; ORGANIC SOLVENTS; REACTION KINETICS;

GAUSSIAN 98; IONIC LIQUID; L-PROLINE; SOLVATION ENERGIES; THE KNOEVENAGEL CONDENSATION;

FLUID DYNAMICS;

EID: 33646880434     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.03.035     Document Type: Article

References (38)

1. Tietze L.F., and Beifuss U. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 2 (1991), Pergamon Press, Oxford
2. Laszlo P. Acc. Chem. Res. 19 (1986) 121
3. Cabello J.A., Campelo J.M., Carcia A., Luna D., and Marinas J.M. J. Org. Chem. 49 (1984) 5195
4. Loupy A. Top. Curr. Chem. 206 (1999) 153
5. Loupy A., Song S.J., Sohn S.M., Lee Y.M., and Kwon T.M. J. Chem. Soc. Perkin Trans. 1 10 (2001) 1220
6. de la Cruz P., Diez-Barra E., Loupy A., and Langa F. Tetrahedron Lett. 37 (1996) 1113
7. Mitra A.K., De A., and Karchaudhuri N. Synth. Commun. 29 (1999) 2731
8. Kwon P.S., Kim Y.M., Kang C.J., Kwon T.W., Chung S.K., and Chang Y.T. Synth. Commun. 27 (1997) 4091
9. Loh T.P., Feng L.C., Yang H.Y., and Yang J.Y. Tetrahedron Lett. 43 (2002) 8741
10. Brindaban C.R., Ranjan J., and Suvendu S.D. Chem. Lett. 33 (2004) 274
11. Ildiko M., and Taeboen O. Tetrahedron Lett. 44 (2003) 6465
12. Helen L.N., Aiguo H., and Wenbin L. Tetrahedron Lett. 46 (2005) 595
13. Morrison D.W., Forbes D.C., and Davis J.H. Tetrahedron Lett. 42 (2001) 6053
14. Harjani J.R., Nara S.J., and Salunkhe M.M. Tetrahedron Lett. 43 (2002) 1127
15. Cardillo G., Fabbroni S., and Gentilucci L. Synth. Commun. 33 (2003) 1587
16. List B., Pojarliev P., and Martin H. J. Org. Lett. 3 (2001) 2423
17. Hayashi Y., Tsuboi W., Shoji M., and Suzuki N. J. Am. Chem. Soc. 125 (2003) 11208
18. Notz W., Tanaka F., Watanable S., and Barbas III C.F. J. Org. Chem. 68 (2003) 9624
19. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
20. Suarez P.A.Z., Dullius J.E.L., Einloft S., de Souza R.F., and Dupont J. Polyhedron 15 (1996) 1217
21. Bonhote P., Dias A.-P., Papageorigu N., Kalyanasundaram K., and Gratzel M. Inorg. Chem. 35 (1996) 1168
22. Seddon K.R., Stark A., and Torres M.-J. Pure Appl. Chem. 72 (2000) 2275
23. Owens G.S., and Abu-Omer M.M. J. Mol. Catal. A: Chem. 187 (2002) 215
24. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B.G., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98 (1998), Gaussian Inc., Pittsburgh, PA
25. Ditchfield R., Hehre W.J., and Pople J.A. J. Phys. Chem. 54 (1971) 724
26. Hehre W.J., Ditchfield R., and Pople J.A. J. Phys. Chem. 56 (1972) 2257
27. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
28. Becke A.D. J. Chem. Phys. 98 (1993) 1372
29. Becke A.D. J. Chem. Phys. 98 (1993) 5648
30. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. J. Phys. Chem. 98 (1994) 11623
31. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1987) 785
32. Bahmanyar S., Houk K.N., Matin H.J., and List B. J. Am. Chem. Soc. 125 (2003) 2475
33. Arnó M., and Domingo L.R. Theor. Chem. Acc. 108 (2002) 232
34. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 12911
35. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 11273
36. Gröger H., and Wilken J. Angew. Chem. Int. Ed. 40 (2001) 529
37. Sekiguchi Y., Sasaoka A., Shimomoto A., Fujioka S., and Kotsuki H. Synlett (2003) 1655
38. List B., Pojarliev P., and Castello C. Org. Lett. 3 (2001) 573