Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series

Tetrahedron

Volumn 60, Issue 14, 2004, Pages 3243-3249

  Buscemi, Silvestre ^a   D'Auria, Maurizio ^b   Pace, Andrea ^a   Pibiri, Ivana ^a   Vivona, Nicolò ^a  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

1,2,4 Oxadiazole; Ab initio calculations; Heterocycles; Photochemistry; Photoisomerization

Indexed keywords

OXADIAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; IRRADIATION; ISOMERIZATION; LIGHT; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 1642391864     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.02.007     Document Type: Article

References (23)

1. Lablache-Combier A. Buchardt O. Photochemistry of heterocyclic compounds. 1976;Wiley, New York.
2. Padwa A. De Mayo P. Rearrangements in ground and excited states. Vol. 3:1980;501 Academic Press, New York.
3. Lablache-Combier A. Horspool W. CRC handbook of organic photochemistry and photobiology. 1995;1063 CRC, Boca Raton, FL.
4. See, e.g. (a) Baltrop J.A., Day A.C., Mack A.G., Shahrisa A., Wakamatsu S. J. Chem. Soc., Chem. Commun. 1981;604-606.
5. Pavlik J.W., Kurzweil E.M. J. Org. Chem. 56:1991;6313-6320.
6. Maeda M., Kojima M. J. Chem. Soc., Perkin Trans. 1. 1977;239-247.
7. Tanaka H., Matsushita T., Nishimoto K. J. Am. Chem. Soc. 105:1983;1753-1760.
8. Pavlik J.W., Tongcharoensirikul P. J. Org. Chem. 65:2000;3626-3632.
9. D'Auria M. Internet J. Sci. 4:1997;15-26.
10. D'Auria M. Heterocyles. 50:1999;1115-1135.
11. D'Auria M. Attanasi O.A., Spinelli D. Targets in heterocyclic systems, chemistry and properties. Vol. 2:1999;233 Italian Society of Chemistry, Rome.
12. D'Auria M. Adv. Heterocycl. Chem. 79:2001;41-88.
13. D'Auria M. J. Org. Chem. 65:2000;2494-2498.
14. D'Auria M. J. Photochem. Photobiol., A: Chem. 149:2002;31-37.
15. D'Auria M. Tetrahedron. 58:2002;8037-8042.
16. D'Auria M., Racioppi R. Lett. Org. Chem. 149:2004;12-19.
17. Buscemi S., Cicero M.G., Vivona N., Caronna T. J. Chem. Soc., Perkin Trans. 1. 1988;1313-1315.
18. Buscemi S., Cicero M.G., Vivona N., Caronna T. J. Heterocycl. Chem. 25:1988;931-935.
19. Buscemi S., Pace A., Vivona N., Caronna T. J. Heterocycl. Chem. 38:2001;777-780.
20. For excellent work on TEA-assisted ring-phototransposition in the isothiazole series, see also: Pavlik J.W., Tongcharoensirikul P., French K.M. J. Org. Chem. 63:1998;5592-5603.
21. Buscemi S., Pace A., Pibiri I., Vivona N. J. Org. Chem. 67:2002;6253-6255.
22. Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N.; Caronna, T. J. Fluorine Chem. in press.
23. 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.; Ciolslowski, 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.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.