Exploration of pericyclic reaction transition structures by quantum mechanical methods: Competing concerted and stepwise mechanisms

Journal of Molecular Structure: THEOCHEM

Volumn 398-399, Issue , 1997, Pages 169-179

  Houk, K N ^a   Beno, Brett R ^a   Nendel, Maja ^a   Black, Kersey ^a   Yoo, Hi Young ^a   Wilsey, Sarah ^a   Lee, Jeehiun K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

B3LYP; Cycloadditions; DFT calculations; Diradical intermediates; Sigmatropic shifts; Transition structures

Indexed keywords

EID: 30244518651     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(96)04970-6     Document Type: Article

References (35)

1. R.B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York, 1966.
2. K.N. Houk, Y. Li and J.D. Evanseck, Angew. Chem., 104 (1992) 711-739; Int. Ed. Engl., 31 (1992) 682-708.
3. K.N. Houk, Y. Li and J.D. Evanseck, Angew. Chem., 104 (1992) 711-739; Int. Ed. Engl., 31 (1992) 682-708.
4. K.N. Houk, J. Gonzalez and Y. Li, Acc. Chem. Res., 28 (1995) 81-90.
5. Y. Li and K.N. Houk, J. Am. Chem. Soc., 115 (1993) 7478-7485.
6. E. Goldstein, B.R. Beno and K.N. Houk, J. Am. Chem. Soc., 118 (1996) 6036-6043, and references therein.
7. (a) K.E. Edgecombe and A.D. Becke, Chem. Phys. Lett., 244 (1995) 427-432;
8. (b) C.J. Cramer and B.A. Smith, J. Phys. Chem., 100 (1996) 9664-9670.
9. (a) J.A. Pople, P.M.W. Gill and N.C. Handy, Int. J. Chem., 56 (1995) 303-305;
10. (b) W. Chen and H.B. Schlegel, J. Chem. Phys., 101 (1994) 5957-5968.
11. D.A. Singleton and A.A. Thomas, J. Am. Chem. Soc., 117 (1995) 9357.
12. B.R. Beno, K.N. Houk and D.A. Singleton, J. Am. Chem. Soc., 110 (1996) 9904-9905.
13. B.A. Horn, J.L. Herek and A.H. Zewail, J. Am. Chem. Soc., 110 (1996) 8755-8756.
14. B. Jursic and Z. Zdravkovski, J. Chem. Soc., Perkin Trans., 2 (1995) 1223; B.S. Jursic. J. Mol. Struct. (Theochem), 358 (1995) 139;
15. B. Jursic and Z. Zdravkovski, J. Chem. Soc., Perkin Trans., 2 (1995) 1223; B.S. Jursic. J. Mol. Struct. (Theochem), 358 (1995) 139;
16. (a) W.C. Herndan, W.B. Cooper, Jr, and M.J. Chambers, J. Phys. Chem., 68 (1964) 2016-2018;
17. (b) J.J. Kiefer, S.S. Kumaran and S. Sundaram, J. Chem. Phys., 99 (1993) 3531-3541;
18. (c) J.R. Barker and G.D. King, J. Chem. Phys., 103 (1995) 4953-4966;
19. (d) R. Walsh and J.M. Wells, J. Chem. Soc., Perkin Trans., 2 (1976) 52.
20. W.V.E. Doering, W.R. Roth, R. Breuckmann, L. Figge, H.-W. Lennartz, W.-D. Fessner and H. Prinzbach, Chem. Ber., 121 (1988) 1-9.
21. C. Doubleday, Jr, J. Am. Chem. Soc., 115 (1993) 11968-11 983.
22. F. Bernardi, A. Bottani, P Celani, M. Olivucci, M.A. Robb and A. Venturini, Chem. Phys. Lett., 192 (1992) 229-235.
23. M. Nendel, O. Wiest and K.N. Houk, unpublished results.
24. D.A. Hrovat, K. Morokuma and W.T. Borden, J. Am. Chem. Soc., 116 (1994) 1072.
25. P.M. Kozlowski, M. Dupuis and E.R. Davidson, J. Am. Chem. Soc., 117 (1995) 774.
26. W.T. Borden and E.R. Davidson, Acc. Chem. Res., 29 (1996) 67.
27. W. von E. Doering, V.G. Toscano and G.H. Beasley Tetrahedron, 27 (1971) 5299.
28. K.A. Dykstra, PhD dissertation, Ohio University (1972).
29. W.E. Huntsman and H.J. Wristers, J. Am. Chem. Soc., 89 (1967) 342.
30. H. Hopf, Tetrahedron Lett., 34 (1972) 3571.
31. O. Wiest and K.N. Houk, Topics in Current Chemistry, 183 (1996) 1-24.
32. O. Wiest, K.A. Black and K.M. Houk, J. Am. Chem. Soc., 116 (1994) 10336-10337.
33. O. Wiest, K.A. Black and K.N. Houk, J. Am. Chem. Soc., 117 (1995) 8594-8599.
34. K. Hafner, H.J. Lindner, W. Luo, K.-P. Meinhardt and T. Zink, Pure Appl. Chem., 65 (1993) 17-25.
35. J. Fennen, K. Hafner, H.J. Lindner, B. Beno, K. Nakamura and K.N. Houk, in preparation.