Regioselective epoxide ring-opening using boron trifluoride diethyl etherate: DFT study of an alternative mechanism to explain the formation of syn-fluorohydrins

Journal of Molecular Structure: THEOCHEM

Volumn 904, Issue 1-3, 2009, Pages 21-27

  Saenz Méndez, Patricia ^a   Cachau, Raúl E ^a,b   Seoane, Gustavo ^a   Ventura, Oscar N ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b SAIC FREDERICK INC   (United States)

Author keywords

DFT; Epoxide ring opening; Fluorohydrins; Reaction mechanisms

Indexed keywords

EID: 84962051521     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.02.023     Document Type: Article

References (44)

1. Parker R.E., and Isaacs N.S. Chem. Rev. 59 (1959) 737
2. Gorzynski Smith J. Synthesis. 8 (1984) 629
3. Xiong C., Wang W., Cai C., and Hruby V.J. J. Org. Chem. 67 (2002) 1399
4. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem. Int. Ed. 40 (2005) 2004
5. Hudlicky T., Rulin F., Tsunoda T., Luna H., Andersen C., and Price J.D. Isr. J. Chem. 31 (1991) 229
6. Nugent T., and Hudlicky T. J. Org. Chem. 58 (1998) 985
7. Hudlicky T., Rouden J., and Luna H. J. Org. Chem. 58 (1993) 985
8. Hudlicky T., Rouden J., Luna H., and Allen S. J. Am. Chem. Soc. 116 (1994) 5099
9. Prestat G., Baylon C., Heck M.-P., and Miokowski C. Tetrahedron Lett. 41 (2000) 3829
10. Coxon J.M., Thorpe A.J., and Smith W.B. J. Org. Chem. 64 (1999) 9575
11. Kita Y., Yoshida Y., Kitagaki S., Mihara S., Fang D.-F., Furukawa A., Higuchi K., and Fujioka H. Tetrahedron 55 (1999) 4979
12. Coxon J.M., and Thorpe A.J. J. Org. Chem. 65 (2000) 8421
13. Hara N., Mochizuki A., Tatara A., and Fujimoto Y. Tetrahedron: Asymmetry 11 (2000) 1859
14. Bhatia K.A., Eash K.J., Leonard N.M., Oswald M.C., and Mohan R.S. Tetrahedron Lett. 42 (2001) 8129
15. P. Saenz Méndez, R.E. Cachau, G. Seoane, O.N. Ventura, unpublished results.
16. Bowers A., and Ringold H.J. Tetrahedron 3 (1958) 14
17. Bowers A., Cuéllar Ibáñez L., and Ringold H.J. Tetrahedron 7 (1959) 138
18. Hudlicky T., Luna H., Olivo H.F., Andersen C., Nugent T., and Price J.D. J. Chem. Soc. Perkin Trans. 1 (1991) 2907
19. Takaishi N., Takahashi H., and Inamoto Y. Tetrahedron Lett. 26 (1985) 2361
20. Islas-González G., Puigjaner C., Vidal-Ferran A., Moyano A., Riera A., and Pericàs M.A. Tetrahedron Lett. 45 (2004) 6337
21. Corey E.J. Tetrahedron Lett. 23 (1982) 4217
22. Haufe G. J. Fluorine Chem. 125 (2004) 875
23. Akiyama Y., Hiramatsu C., Fukuhara T., and Hara S. J. Fluorine Chem. 127 (2006) 920
24. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford Science Publications, Oxford
25. Perdew J.P., Burke K., and Ernzerhoff M. Phys. Rev. Lett. 77 (1996) 3865
26. Perdew J.P., Burke K., and Ernzerhoff M. Phys. Rev. Lett. 78 (1997) 1396
27. Hehre W.J., Radom L., Schleyer P.V.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
28. Jensen F. Introduction to Computational Chemistry (1999), Wiley, Chichester, West Sussex, England
29. Foresman J.B., and Frisch Æ. Exploring Chemistry with Electronic Structure Methods (1996), Gaussian, Inc., Pittsburgh, PA
30. Carpenter J.E., and Weinhold F. J. Mol. Struct. (Theochem) 169 (1988) 41
31. Foster J.P., and Weinhold F. J. Am. Chem. Soc. 102 (1980) 7211
32. Reed A.E., and Weinhold F. J. Chem. Phys. 78 (1983) 4066
33. Reed A.E., and Weinhold F. J. Chem. Phys. 83 (1985) 1736
34. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735
35. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
36. Weinhold F., and Carpenter J.E. The structure of small molecules and ions (1988), Plenum Press, New York
37. Breneman C.M., and Wiberg K.B. J. Comput. Chem. 11 (1990) 361
38. Wiberg K.B., and Rablen P.R. J. Comput. Chem. 14 (1993) 1504
39. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
40. Tomasi J., and Perisco M. Chem. Rev. 94 (1994) 2027
41. Miertus S., and Tomasi J. J. Chem. Phys. 65 (1982) 239
42. Barone V., Cossi M., and Tomasi J. J. Comput. Chem. 19 (1998) 404
43. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, B. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, A.J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malik, A.D. Rabuk, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
44. Blackett B.N., Coxon J.M., Hartshorn M.P., and Richards K.E. J. Am. Chem. Soc. 92 (1970) 2574