A theoretical study of the influence of BF3 on the reaction path of the [4+2] cycloaddition of vinylketene with formaldimine

Tetrahedron

Volumn 63, Issue 47, 2007, Pages 11617-11621

  Peña Gallego, Angeles ^a   Rodríguez Otero, Jesús ^a   Cabaleiro Lago, Enrique M ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Aromaticity; Density functional calculations; Pericyclic reactions; Pseudopericyclic reactions; Reaction mechanisms

Indexed keywords

FORMALDIMINE; IMINE; KETENE DERIVATIVE; UNCLASSIFIED DRUG; VINYLKETENE;

ANISOTROPY; ANISOTROPY OF THE CURRENT INDUCED DENSITY; AROMATIZATION; ARTICLE; CYCLOADDITION; MAGNETISM; NUCLEUS INDEPENDENT CHEMICAL SHIFT; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE; THEORETICAL STUDY;

EID: 35148823132     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.005     Document Type: Article

References (38)

1. Tidwell T.T. Ketenes (1995), John Wiley and Sons, New York, NY
2. Staudinger H. Chem. Ber. 38 (1905) 1735
3. Georg G.I. The Organic Chemistry of β-Lactams (1992), VCH, New York, NY
4. Machiguchi T., Hasegawa T., Ishiwata A., Terashima S., Yamabe S., and Minato T. J. Am. Chem. Soc. 121 (1999) 4771
5. Zhou C., and Birney D.M. J. Am. Chem. Soc. 124 (2002) 5231
6. Peña-Gallego A., Rodriguez-Otero J., and Cabaleiro-Lago E.M. Tetrahedron 63 (2007) 4937
7. Ross J.A., Seiders R.P., and Lemal D.M. J. Am. Chem. Soc. 98 (1976) 4325
8. Bushweller C.H., Ross J.A., and Lemal D.M. J. Am. Chem. Soc. 99 (1977) 629
9. Birney D.M., and Wagenseller P.E. J. Am. Chem. Soc. 116 (1994) 6262
10. Birney D.M. J. Org. Chem. 61 (1996) 243
11. Birney D.M., Ham S., and Unruh G.R. J. Am. Chem. Soc. 119 (1997) 4509
12. Birney D.M., Xu X., and Ham S. Angew. Chem., Int. Ed. 38 (1999) 189
13. Birney D.M. J. Am. Chem. Soc. 122 (2000) 10917
14. Shumway W., Dalley N.K., and Birney D.M. J. Org. Chem. 66 (2001) 5832
15. Shumway W., Ham S., Moer J., Whittlesey B.R., and Birney D.M. J. Org. Chem. 65 (2000) 7731
16. de Lera A.R., Alvarez R., Lecea B., Torrado A., and Cossio F.P. Angew. Chem., Int. Ed. 40 (2001) 557
17. Zimmerman H.E. Acc. Chem. Res. 4 (1971) 272
18. Herges R., Jiao H., and Schleyer P.v.R. Angew. Chem., Int. Ed. Engl. 33 (1994) 1376
19. Jiao H., and Schleyer P.v.R. J. Phys. Org. Chem. 11 (1998) 655
20. Manoharan M., De Proft F., and Geerlings P. J. Org. Chem. 65 (2000) 7971
21. Manoharan M., De Proft F., and Geerlings P. J. Chem. Soc., Perkin Trans. 2 (2000) 1767
22. Peña-Gallego A., Rodriguez-Otero J., and Cabaleiro-Lago E.M. J. Org. Chem. 69 (2004) 7013
23. Peña-Gallego A., Rodriguez-Otero J., and Cabaleiro-Lago E.M. Eur. J. Org. Chem. (2005) 3228
24. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H., and Hommes N.J.R.v.E. J. Am. Chem. Soc. 118 (1996) 6317
25. Herges R., and Geuenich D. J. Phys. Chem. A 105 (2001) 3214
26. Rodriguez-Otero J., Cabaleiro-Lago E.M., Hermida-Ramon J.M., and Peña-Gallego A. J. Org. Chem. 68 (2003) 8823
27. Kimball D.B., Weakley T.J.R., Herges R., and Haley M.M. J. Am. Chem. Soc. 124 (2002) 13463
28. Herges R., and Papafilippopoulos A. Angew. Chem., Int. Ed. 40 (2001) 4671
29. Becke A.D. J. Chem. Phys. 98 (1993) 5648
30. Lee C., Yang W., and Parr R.J. Phys. Rev. B 37 (1988) 785
31. Fukui K. Acc. Chem. Res. 14 (1981) 363
32. Gonzalez C., and Schlegel H.B. J. Chem. Phys. 90 (1989) 2154
33. Gonzalez C., and Schlegel H.B. J. Phys. Chem. 94 (1990) 5223
34. Wolinski K., Hilton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
35. Keith T.A., and Bader R.F.W. Chem. Phys. Lett. 210 (1993) 223
36. Keith T.A., and Bader R.F.W. Chem. Phys. Lett. 194 (1992) 1
37. Cheeseman J.R., Frisch M.J., Trucks G.W., and Keith T.A. J. Chem. Phys. 104 (1996) 5497
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, 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.; Pople, J. A. Gaussian: Pittsburgh, PA, 1998.