Theoretical Study of the Fragmentation of the β-Lactam Ring: Ozonolysis of 3-Methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone

Journal of Physical Chemistry A

Volumn 107, Issue 47, 2003, Pages 10171-10176

  Ardura, Diego ^a   Sordo, Tomás L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HYBRID EXCHANGE POTENTIAL; INTERACTION ENERGY;

AMINES; ELECTRON ENERGY LEVELS; ETHERS; GIBBS FREE ENERGY; ISOMERS; MOLECULAR VIBRATIONS; OZONE; PERMITTIVITY; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PROPYLENE;

EID: 0344553242     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp035796d     Document Type: Article

References (26)

1. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
2. Ojima, I.; Hatanaka, N. J. Synth. Org. Chem., Jpn. 1982, 40, 209.
3. Ojima, I. In Asymmetric Reactions and Processes in Chemistry; Eliel, E. L., Otsuka, S., Eds.; ACS Symposium Series 185; American Chemical Society: Washington, DC, 1982: pp 109-138.
4. Wasserman, H. H.; Leadbetter, M. R.; Kopka, I. E. Tetrahedron Lett. 1984, 25, 2391. Wasserman, H. H.; Robinson, R. T. Tetrahedron Lett. 1983, 24, 3669. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465. Wasserman, H. H.; Matsuyama, H. J. Am. Chem. Soc. 1981, 103, 461. Sagarovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1991, 253, 792.
5. Wasserman, H. H.; Leadbetter, M. R.; Kopka, I. E. Tetrahedron Lett. 1984, 25, 2391. Wasserman, H. H.; Robinson, R. T. Tetrahedron Lett. 1983, 24, 3669. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465. Wasserman, H. H.; Matsuyama, H. J. Am. Chem. Soc. 1981, 103, 461. Sagarovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1991, 253, 792.
6. Wasserman, H. H.; Leadbetter, M. R.; Kopka, I. E. Tetrahedron Lett. 1984, 25, 2391. Wasserman, H. H.; Robinson, R. T. Tetrahedron Lett. 1983, 24, 3669. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465. Wasserman, H. H.; Matsuyama, H. J. Am. Chem. Soc. 1981, 103, 461. Sagarovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1991, 253, 792.
7. Wasserman, H. H.; Leadbetter, M. R.; Kopka, I. E. Tetrahedron Lett. 1984, 25, 2391. Wasserman, H. H.; Robinson, R. T. Tetrahedron Lett. 1983, 24, 3669. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465. Wasserman, H. H.; Matsuyama, H. J. Am. Chem. Soc. 1981, 103, 461. Sagarovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1991, 253, 792.
8. Wasserman, H. H.; Leadbetter, M. R.; Kopka, I. E. Tetrahedron Lett. 1984, 25, 2391. Wasserman, H. H.; Robinson, R. T. Tetrahedron Lett. 1983, 24, 3669. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465. Wasserman, H. H.; Matsuyama, H. J. Am. Chem. Soc. 1981, 103, 461. Sagarovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1991, 253, 792.
9. Alcaide B.; Miranda, M.; Pérez-Castells, J.; Sierra, M. A. J. Org. Chem. 1993, 58, 297.
10. Alcaide, B.; Pérez-Castells, Polanco, C.; Sierra, M. A. J. Org. Chem. 1995, 60, 6012.
11. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98; Gaussian, Inc.: Pittsburgh, PA, 1998.
12. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
13. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
14. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
15. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory; John Wiley & Sons Inc.: New York, 1986.
16. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
17. Olzmann, M.; Kraka, E.; Cremer, D.; Gutbrod, R.; Andersson, S. J. Phys. Chem. A 1997, 101, 9421-9429.
18. Gutbrod, R.; Kraka, E.; Schindler, R. N.; Crerner, D. J. Am. Chem. Soc. 1997, 119, 7330-7342.
19. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
20. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
21. IRC calculations from TS1011 failed. However, the connection between this TS and M10 and M11 intermediates was checked by relocating TS1011 from these intermediates using the QST2 method.
22. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976.
23. Rivail, J. L.; Rinaldi, D.; Ruiz-López, M. F. In Theoretical and Computational Model for Organic Chemistry; Formosinho, S. J., Csizmadia, I. G., Arnaut, L., Eds.: NATO ASI Series C.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991; Vol. 339, pp 79-92.
24. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
25. (b) Cammi, R.; Tomasi, J. J. Comput. Chem. 1995, 16, 1449-1458.
26. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161-2200.