Theoretical Studies of the Electrocyclic Reaction Mechanisms of o-Xylylene to Benzocyclobutene

Journal of Physical Chemistry A

Volumn 104, Issue 49, 2000, Pages 11615-11621

  Sakai, Shogo ^a  

^a OSAKA SANGYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000148946     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0024017     Document Type: Article

References (35)

1. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew, Chem., Int. Ed. Engl. 1992, 31, 682.
2. Houk, K. D.; Gonzalez, J.; Li, Y. Acc, Chem. Res. 1995, 28, 81.
3. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry, Verlag: Weinheim, Germany, 1970.
4. Fukui, K. Acc. Chem. Res. 1971, 4, 57.
5. Sakai, S. J. Mol. Struct. (THEOCHEM) 1999, 461-462, 283.
6. Sakai, S.; Takane, S. J. Phys. Chem, A 1999, 103, 2878.
7. Jefford, C. D.; Bernardineili, G.; Wang, Y.; Spellmeyer, D. C.; Buda, A.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 4, 1157.
8. Roos, B. In Advances in chemical physic; Lawley, K. P., Ed.; Wiley: New York, 1987; Vol. 69, Part II, p 399.
9. Haviharan, P. C.; Polple, J. A. Theor, Chim. Acta 1973, 28, 213.
10. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
11. McDouall, J. J.; Peasley, K.; ROOD, M. A. Chem. Phys. Lett. 1988, 148, 183.
12. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
13. Fukui, K. J. Phys. Chem. 1970, 74, 4161.
14. Ishida, K.; Morokuma, K.; Komornicki, A. J. Chem. Phys. 1977, 66, 2153.
15. Cundari, T. R.; Gordon, M. S. J. Am. Chem. Soc. 1991, 113, 5231.
16. Sakai, S. J. Phys. Chem. A 1997, 101, 1140.
17. Nguyen, T. R.; Chandra, A. K.; Sakai, S.; Morokuma, K. J. Org. Chem. 1999, 64, 65.
18. Sakai, S. J. Phys. Chem. A 2000, 104, 922.
19. Sakai, S. Int. J. Quantum Chem. 2000, 80, 1099.
20. Foster, J. M.; Boys, S. F. Rev. Mod. Phys. 1960, 32, 296, 300.
21. Bernardi, F.; Olivucci, M.; McDouall, J. J. W.; Robb, M. A. J. Chem. Phys. 1988, 89, 6365.
22. Bernardi, F.; Olivucci, M.; Robb, M. A. Acc. Chem. Res. 1990, 23, 405.
23. Formosinho, S.; Csizmadia, I. G.; Arnaut, L. G. Theoretical and Computational Methods for Organic Chemistry; Kluwer Academic Publisher: Norwell, MA, 1991, pp 289-313.
24. Schmidt, M. W.; Buldridge, K. K.; Boatz, J. A.; Jensen, J. H.; Koseki, S.; Gordon, M. S.; Nguyen, K. A.; Windus, T. L.; Elbert, S. T. QCPE Bull. 1990, 10, 52.
25. Frisch, K. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cislowski, 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.; Comperts, 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. GAUSSIAN98; Gaussian, Inc.; Pittsburgh, PA, 1998.
26. Miller, R. D.; Kolc, J.; Michl, J. J. Am. Chem. Soc. 1976, 98, 8510.
27. Flynn, C. R.; Michl, J. J. Am. Chem. Soc. 1974, 96, 3280.
28. Barton, J. W. Ann. Rep. Prog. 1970, 70, 405.
29. Tewson, T. J. Ann. Rep. Prog. 1974, 71, 299.
30. Dolbier, W. R., Jr.; McCullagh, D. R.; Robinson, D.; Anapolle, K. E. J. Am. Chem. Soc. 1975, 97, 934.
31. Migirdicyan, E.; Bandet, J. J. Am. Chem. Soc. 1975, 97, 7400.
32. Roth, W. R.; Biermann, M.; Dekker: H.; Jochems, R.; Mosselman, C.; Hermann, H. Chem. Ber. 1978, 111, 3892.
33. Roth, W. R.; Scholz, B. P. Chem. Ber. 1981, 114, 3741.
34. Munzel, N.; Schweig, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 471.
35. The planarization of the structure could not rigorously separate the orbital and structural components of the barrier. In qualitative terms, however, we can understand the nature of the barrier.