Photochemical ring-opening and intramolecular hydrogen shift reactions in sulfur analogues of α-pyrone

Journal of Physical Chemistry A

Volumn 110, Issue 20, 2006, Pages 6415-6425

  Breda, S ^a   Reva, I ^a   Lapinski, L ^a,b   Cristiano, M L S ^c   Frija, L ^a,c   Fausto, R ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b INSTITUTE OF PHYSICS   (Poland)

^c UNIVERSITY OF ALGARVE   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; FOURIER TRANSFORM INFRARED SPECTROSCOPY; IRRADIATION; ISOMERIZATION; MONOMERS; REACTION KINETICS; SULFUR COMPOUNDS; THERMAL EFFECTS; ULTRAVIOLET RADIATION;

INTRAMOLECULAR HYDROGEN SHIFT REACTIONS; PHOTOPROCESSES; RING-OPENING PHOTOREACTION; VIBRATIONAL SPECTRA;

PHOTOCHEMICAL REACTIONS;

EID: 33745766491     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp061139k     Document Type: Article

References (35)

1. Chapman, O. L.; McIntosh, C. L.; Pacansky, J. J. Am. Chem, Soc. 1973, 95, 244.
2. Chapman, O. L.; McIntosh, C. L.; Pacansky, J. J. Am. Chem. Soc. 1973, 95, 614.
3. Pong, R. G. S.; Shirk, J. S. J. Am. Chem. Soc. 1973, 95, 248.
4. Pong, R. G. S.; Huang, B. S.; Laureni, J.; Krantz, A. J. Am. Chem. Soc. 1977, 99, 4153.
5. Breda, S.; Reva, I.; Lapinski, L.; Fausto, R. Phys. Chem. Chem. Phys. 2004, 6, 929.
6. Breda, S.; Lapinski, L.; Reva, I.; Fausto, R. J. Photochem. Photobiol., A 2004, 162, 139.
7. Breda, S.; Lapinski, L.; Fausto, R.; Nowak, M. J. Phys. Chem. Chem. Phys. 2003, 5, 4527.
8. Turro, N. J. In Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991; Chapter 13, p 526.
9. Klessinger, M.; Michl, J. In Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995; Chapter 7.2.1, p 380.
10. Seixas de Melo, J.; Quinteiro, G.; Pina, J.; Breda, S.; Fausto, R. J. Mol. Struct. 2001, 59, 565.
11. Lapinski, L.; Nowak, M. J.; Les, A.; Adamowicz, L. J. Am. Chem. Soc. 1994, 116, 1461.
12. Lapinski, L.; Rostkowska, H.; Khvorostov, A.; Fausto, R.; Nowak, M. J. J. Phys. Chem. A 2003, 107, 5913.
13. Breda, S.; Reva, I.; Lapinski, L.; Fausto, R. Chem. Phys. Chem. 2005, 6, 602.
14. Defoin, A.; Augelmann, G.; Fritz, H.; Geffroy, G.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1985, 68, 1998.
15. Reva, I.; Breda, S.; Roseiro, T.; Eusébio, E.; Fausto, R. J. Org. Chem. 2005, 70, 7701.
16. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
17. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
18. Schachtschneider, J. H. Technical Report; Shell Development Co.: Emeryville, CA, 1969.
19. 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
20. Michaut, X.; Vasserot, A.-M.; Abouaf-Marguin, L. Vib. Spectrosc. 2004, 34, 83.
21. Fausto, R.; Quinteiro, G.; Breda, S. J. Mol. Struct. 2001, 598, 287.
22. Schriver, A; Schriver-Mazzuoli, L.; Vigasin, A. A. Vib. Spectrosc. 2000, 23, 83.
23. Birney, D. M. J. Org. Chem. 1996, 61, 243.
24. Huang, B. S.; Pong, R. G. S.; Laureni, J.; Krantz, A. J. Am. Chem. Soc. 1977, 99, 4154.
25. Pirkle, W. H.; Turner, W. V. J. Org. Chem. 1975, 40, 1617.
26. Pirkle, W. H.; Turner, W. V. J. Org. Chem. 1975, 40, 1644.
27. Pirkle, W. H.; Dines, M. J. Am. Chem. Soc. 1968, 90, 2318.
28. Fausto, R. Analise Conformacional em Compostes de Oxigénio e Enxofre. Ph.D. Thesis, Department of Chemistry, University of Coimbra, Coimbra, 1987.
29. Fausto, R.; Teixeira-Dias, J. J. C.; Carey, P. R. THEOCHEM 1988, 168, 179.
30. Pederson, C. T.; Wong, M. W.; Flammang, R. J. Chem. Soc., Perkin Trans. 2 2001, 2047.
31. Krantz, A.; Laureni, J. J. Am. Chem. Soc. 1981, 103, 486.
32. Crovisier, J. Constants for Molecules of Astrophysical Interest in the Gas phase: Photodissociation, Microwave and Infrared Spectra", Appendix: Vibrational Bands Sorted by Increasing Wavenumbers; Laboratoire d'études spatiales et d'instrumentation en astrophysique, Observatoire de Paris-Meudon, F-9219S Meudon, France, 2002.
33. Torres, M.; Safarik, I.; Clement, A.; Gosavi, R. K.; Strausz, O. P. Can. J. Chem. 1984, 62, 2777.
34. Sung, K.; Fang, D.-C; Glenn, D.; Tidwell, T. T. J. Chem. Soc., Perkin Trans. 2 1998, 2073.
35. Quinkert, G. Pure Appl. Chem. 1973, 33, 285.