Theoretical analysis of the regioselectivity of 1,3-dipolar cycloaddition of C-(methoxycarbonyl)-N-methyl with methyl acrylate and vinyl acetate

Journal of Molecular Structure: THEOCHEM

Volumn 852, Issue 1-3, 2008, Pages 46-53

  Benchouk, W ^a   Mekelleche, S M ^a  

^a UNIVERSITY OF TLEMCEN   (Algeria)

Author keywords

1,3 Dipolar cycloaddition; B3LYP calculations; DFT based reactivity indices; FMO theory; Nitrone; Regioselectivity

Indexed keywords

EID: 39949085590     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.12.035     Document Type: Article

References (56)

1. K.V. Gothelf K.A. Jorgensen Chem. Rev. 98 1998 863
2. (a) J.J. Tufariello A. Padwa 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York
3. (b) K.B.G. Torssell Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis 1988 VCH New York
4. (c) J.J. Tufariello Acc. Chem. Res. 12 1979 396
5. I. Fleming Frontiers Orbitals and Organic Chemical Reactions 1976 Wiley London
6. (a) K. Tanaka T. Imase S. Iwata Bull. Chem. Soc. Jpn. 69 1996 2243
7. (b) I. Morao B. Lecea F.P. Cossıo J. Org. Chem. 62 1997 7033
8. (c) F.P. Cossıo I. Morao H. Jiao P. von R. Schleyer J. Am. Chem. Soc. 121 1999 6737
9. J. Liu S. Niwayama Y. You K.N. Houk J. Org. Chem. 63 1998 1064
10. E.C. Magnusong J. Pranata J. Comput. Chem. 19 1998 1795
11. M.J. Aurell L.R. Domingo P. Perez R. Contreras Tetrahedron 60 2004 11503
12. R. Herrera A. Nagarajan M.A. Morales F. Mendez H.A. Jimenez-Vazquez G. Zepeda J. Tamariz J. Org. Chem. 66 2001 1252
13. A. Brandi S. Cicchi F.M. Cordero A. Goti Chem. Rev. 103 2003 1213
14. J.M. Brunel Chem. Rev. 105 2005 857
15. (a) P. Bravo L. Bruche G. Fronza G. Zecchi Tetrahedron 48 1992 9775
16. (b) Y. Tokunaga M. Ihara K. Fukumoto Tetrahedron Lett. 37 1996 6157
17. (c) C. Ahn J.W. Kennington P. De Shong J. Org. Chem. 59 1994 6282
18. (d) K.B. Jensen R.G. Hazell K.A. Jorgensen J. Org. Chem. 64 1999 2353
19. (e) P. Conti G. Roda F.F.B. Negra Tetrahedron Asymm. 12 2001 1363
20. (f) A. Vasella R. Voeffray Helv. Chim. Acta 65 1982 1134
21. (g) O. Tamura T. Okabe T. Yamaguchi J. Kotani K. Gotanda M. Sakamoto Tetrahedron 51 1995 119
22. (h) O. Tamura N. Mita T. Okabe Y. Yamaguchi C. Fukushima M. Yamashita Y. Morita N. Morita H. Ishibashi M. Sakamoto J. Org. Chem. 66 2001 2602
23. (a) U. Chiacchio A. Corsaro D. Iannazzo A. Piperno A. Rescifina R. Romeo G. Romeo Tetrahedron Lett. 42 2001 1777
24. (b) U. Chiacchio A. Corsaro V. Pistara A. Rescifina D. Iannazzo A. Piperno G. Romeo R. Romeo G. Grassi Eur. J. Org. Chem. 2002 1206
25. (a) Y. Tokunaga M. Ihara K. Fukumoto Tetrahedron Lett. 37 1996 6157
26. (b) U. Chiacchio G. Gumina A. Rescifina R. Romeo N. Uccella F. Casuscelli A. Piperno G. Romeo Tetrahedron 52 1996 8889
27. P. Merino J. Revuelta T. Tejero U. Chiacchio A. Rescifina G. Romeo Tetrahedron 59 2003 3581
28. R.G. Parr W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University Press Oxford
29. P. Hohenberg W. Kohn Phys. Rev. B 136 1964 864
30. R.G. Pearson J. Am. Chem. Soc. 7512 1983 105
31. R.G. Parr L. von Szentpaly S. Liu J. Am. Chem. Soc. 121 1999 1922
32. L.R. Domingo M.J. Aurell P. Perez R. Contreras J. Phys. Chem. A 106 2002 6871
33. R.G. Parr W. Yang J. Am. Chem. Soc. 106 1984 4049
34. P.K. Chattaraj S. Nath A.B. Sannigrahi J. Phys. Chem. 98 1994 9143
35. W. Yang W.J. Mortier J. Am. Chem. Soc. 108 1986 5708
36. J.L. Gazquez F.J. Mendez J. Am. Chem. Soc. 116 1994 9298
37. J.L. Gazquez A. Martinez F. Mendez J. Phys. Chem. 97 1993 4059
38. A.K. Chandra M.T. Nguyen J. Comput. Chem. 19 1998 195
39. A.K. Chandra M.T. Nguyen Int. J. Mol. Sci. 3 2002 310
40. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98 (Revision A.1), Gaussian, Inc., Pittsburgh, PA, 1998.
41. (a) H.B. Schlegel J. Comput. Chem. 3 1982 214
42. (b) H.B. Schlegel Geometry optimization on potential energy surface D.R. Yarkony Modern Electronic Structure Theory 1994 World Scientific Singapore
43. A.E. Reed F. Weinhold J. Chem. Phys. 4066 1983 78
44. B.H. Besler K.M.J. Merz P.A. Kollman J. Comp. Chem. 11 1990 43
45. C.M. Breneman K.B. Wiberg J. Comp. Chem. 11 1990 361
46. L.R. Domingo M.J. Aurell P. Perez R. Contreras Tetrahedron 58 2002 4417
47. P. Perez L.R. Domingo M.J. Aurell R. Contreras Tetrahedron 2003
48. A. Padwa D.N. Kline K.F. Koehler M. Matzinger M.K. Venkatramanan J. Org. Chem. 52 1987 3909
49. (a) P. Grunanger P. Vitafinzi Isoxazoles E.C. Taylor The Chemistry of Heterocyclic Compounds vol. 49 1991 Wiley New York
50. (b) R. Sustmann W. Sicking Chem. Ber. 120 1987 1653
51. (c) L. Fisera M. Konopikova P. Ertl N. Pronayova Monatsh. Chem. 125 1994 301
52. (d) M. Shanmugasundaram R. Raghunathan E. Padma Malar J. Heteroatom. Chem. 9 1998 517
53. (a) R.G. Parr W.T. Yang Annu. Rev. Phys. Chem. 46 1995 701
54. (b) H. Chermette J. Comput. Chem. 20 1999 129
55. (c) P. Geerlings F. De Proft W. Langenaeker Chem. Rev. 103 2003 1793
56. L.R. Domingo M. Jose Aurell P. Perez R. Contreras J. Phys. Chem. A 106 2002 6871