Thermodynamics of Ylide formation from carbenes and carbonyl compounds

Journal of the Brazilian Chemical Society

Volumn 9, Issue 2, 1998, Pages 181-186

  Pliego Jr , Josefredo R ^a   De Almeida, Wagner B ^a  

^a NONE

Author keywords

Ab initio; Carbene carbonyl compounds; Thermodynamics; Ylide formation

Indexed keywords

EID: 0032383824     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/s0103-50531998000200011     Document Type: Article

References (28)

1. Padwa, A..; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
2. Pliego Jr., J.R.; De Almeida, W.B. J. Chem. Phys. 1997, 106, 3582.
3. Yamaguchi, Y.; Schaefer III, H.F.; Alberts, L. J. Am. Chem. Soc. 1993, 115, 5790.
4. Kumar, C.V.; Chattopadhyay, S.K.; Das, P.K. J. Phys. Chem. 1984, 88, 5639.
5. Platz, M.S.; Olson, D.R.; J. Phys. Org. Chem. 1996, 9, 689.
6. Chateauneuf, J.E.; Liu, M.T.H. J. Am. Chem. Soc. 1991, 113, 6585.
7. Bonneau, R.; Liu, M.T.H. J. Am. Chem. Soc. 1990, 112, 744.
8. LaVilla, J.A.; Goodman, J.L. Tetrahedron Lett. 1988, 29, 2623.
9. Soudararajan, N.; Jackson, J.E.; Platz, M.S.; Liu, M.T.H. Tetrahedron Lett. 1988, 29, 3419.
10. Liu, M.T.H.; Soundarajan, N.; Anand, S.M.; Ibata, T. Tetrahedron Lett. 1987, 28, 1011.
11. Ibata, T; Liu, M.T.H.; Toyoda, J. Tetrahedron Lett. 1986, 27, 4383.
12. Prakash, G.K.S.; Ellis, R.W.; Felberg, J.D.; Olah, G.A. J. Am. Chem. Soc. 1986, 108, 1341.
13. Barcus, R.L.; Hadel, L.M.; Johnston, L.J.; Platz, M.S.; Savino, T.G.; Scaiano, J.C. J. Am. Chem. Soc. 1986, 108, 3928.
14. Gisch, J.F.; Landgrebe, J.A. J. Org. Chem. 1985, 50, 2050.
15. Martin, C.W.; Gill, H.S.; Landgreb, J.A. J. Org. Chem. 1983, 48, 1898.
16. Huan, Z.; Landgrebe, J.A.; Peterson, K. J. Org. Chem. 1983, 48, 4519.
17. Martin, C. W.; Lund, P.R.; Rapp, E.; Landgreb, J.A. J. Org. Chem. 1978, 43, 1071.
18. Houk, K.N.; Rondan, N.G.; Santiago, C.; Gallo, C.J.; Gandour, R.W.; Griffin, G.W. J. Am. Chem. Soc. 1980, 102, 1504.
19. Dunning, T.H.; Hay, P.J. In Methods of electronic structure theory, Schaefer III, H.F., Ed., Plenum Press, New York, 1977.
20. Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.; Windus, T.L.; Dupuis, M.; Montgomery Jr., J.A J. Comp. Chem. 1993, 14, 1347.
21. Gaussian 94, Revision D.2, Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.; Petersson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Laham, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Cioslowski, J.; Stefanov, B.B.; Nanayakkara, A.; Challacombe, M.; Peng, C.Y.; Ayala, P.Y.; Chen, W.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Binkley, J.S.; Defrees, D.J.; Baker, J.; Stewart, J.P.; Head-Gordon, M.; Gonzalez, C.; Pople, J.A. Gaussian, Inc., Pittsburgh PA, 1995.
22. Wong, C.; Cheung, C.; Ma, N.; Li, W. J. Chem. Research (S) 1993, 32.
23. Hu, C.; Qing, F.; Shen, C. J. Chem. Soc. Perkin Trans. 1 1993, 335.
24. Couture, P.; Pole, D.L.; Warkentin, J. J. Chem. Soc., Perkin Trans. 2 1997, 1565.
25. Enders, D.; Breuer, K.; Runsink, J.; Teles, J.H. Liebigs Ann. 1996, 2019.
26. Rigby, J.H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
27. Pole, D.L.; Warkentin, J. Liebigs Ann. 1995, 1907.
28. Bauschlicher Jr., C.W.; Langhoff, S.R. J. Chem. Phys. 1987, 87, 387.