Photocyclization mechanism of halopyridinium salt tethered to arene: Flash photolysis observation of a pyridinium σ, cyclohexadienyl radicals, and a dihalide radical anion in aqueous solution

Journal of the American Chemical Society

Volumn 119, Issue 44, 1997, Pages 10677-10683

  Park, Yong Tae ^a   Song, Nam Woong ^b   Hwang, Chul Gyun ^a   Kim, Kwang Wook ^a   Kim, Dongho ^b  

^a Kyungpook National University   (South Korea)

^b Korea Research Institute of Standards and Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; ISOQUINOLINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINIUM DERIVATIVE; RADICAL;

AQUEOUS SOLUTION; ARTICLE; CYCLIZATION; PHOTOLYSIS;

EID: 0030777893     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970425u     Document Type: Article

References (32)

1. Bunce, N. J. In CRC Handbook of organic photochemistry and photobiology; Horspool, W. H., Song, P.-S. Eds.; CRC: New York, 1995; 1181-1192.
2. Kessar, S. V.; Mankotia, A. K. S. In CRC Handbook of organic photochemistry and photobiology, Horspool, W. M., Song, P.-S. Eds.; CRC: New York, 1995; pp 1218-1228.
3. Grimshaw, J. J. Chem. Soc., Chem. Rev. 1981, 10, 181-203.
4. (a) Grimshaw, J.; de Silva, P. A. J. Chem. Soc. 1979, 193-194.
5. (b) Grimshaw, J.; de Silva, P. A. J. Chem. Soc., Chem. Commun. 1980, 302-303.
6. (c) Grimshaw, J.; de Silva, P. A. Can. J. Chem. 1980, 58, 1880-1888.
7. (a) Park, Y.-T.; Lee, I.-H.; Kim, Y.-H. J. Heterocycl. Chem. 1994, 31, 1625-1629.
8. (b) Park, Y.-T.; Kim, Y.-H.; Hwang, C.-G. Bull. Korean Chem. Soc. 1996, 17, 506-510.
9. (a) Forzard, A.; Brasher, C. K. J. Org. Chem. 1967, 32, 2966-2969.
10. (b) Portlock, D. E.; Kane, M. K.; Bristol, J. A.; Lyle, R. E. J. Org. Chem. 1973, 38, 2351-2357.
11. (a) Park, Y.-T.; Joo, C.-H.; Choi, C.-D.; Park, K.-S. J. Heterocycl. Chem. 1991, 28, 1083-1089.
12. (b) Park, Y.-T.; Kim, K.-S.; Lee, I.-H.; Park, Y.-C. Bull. Korean Chem. Soc. 1993, 14, 152-153.
13. (c) Byun, Y.-S.; Jung, C.-H.; Park, Y.-T. J. Heterocycl. Chem. 1995, 32, 1835-1837.
14. Pedersen, C.; Lohse, C. Acta Chim. Scand. B 1979, 33, 649-652.
15. Grimshaw, J.; Trocha-Grimshaw, J. J. Chem. Soc., Chem. Commun. 1984, 744-745.
16. Park, Y.-T.; Song, N. W.; Kim, Y.-H.; Hwang, C.-G.; Kim, S. K.; Kim, D. J. Am. Chem. Soc. 1996, 118, 11399-11405.
17. (a) Previtali, C. M.; Ebbesen, T. W. J. Photochem. 1984, 27, 9-15.
18. (b) Alfassi, Z. B.; Previtali, C. M. J. Photochem. 1985, 30, 127-132.
19. (c) Previtali, C. M.; Ebbensen, T. W. J. Photochem. 1985, 30, 259-267.
20. (a) Smothers, W. K.; Schanze, K. S.; Saltiel, J. J. Am. Chem. Soc. 1979, 101, 1895-1896.
21. (b) Bunce, N. J.; Bergsma, J. P.; Bergsma, M. D.; De Graaf, W.; Kumar, Y.; Ravanal, L. J. Org. Chem. 1980, 45, 3708-3713.
22. The name of dihalide radical anion is used for halogen anion radical. For example, dibromide radical anion is used for bromine anion radical.
23. Chesta, C. A.; Cosa, J. J.; Previtali, C, M. J. Photochem. 1986, 32, 203-215.
24. Chesta, C. A.; Cosa, J. J.; Previtali, C. M. J. Photochem. Photobiol. A. Chem. 1988, 45, 9-15.
25. Bunce, N. J. J. Chem. Soc., Perkin Trans. 1975, 1607-1610.
26. Streitwieser, A.; Healthcook, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed.; Macmillan: New York, 1992; Appendix II.
27. Calvert, J. G.; Pitts, J. N. Photochemistry; John Wiley and Sons: New York, 1966; pp 625-627.
28. (a) Faria, J. L.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 1277-1279.
29. (b) Faria, J. L.; Steenken, S. J. Phys. Chem. 1993, 97, 1924-1930.
30. Shida, T.; Hanazaki, I. Bull. Chem. Soc. Jpn. 1970, 43, 646-651.
31. Anbar, M.; Thomas, J. K. J. Phys. Chem. 1964, 668, 3829-3835.
32. Scaiano, J. C.; Barra, M.; Calabrese, G.; Sinta, R. J. Chem. Soc., Chem. Commun. 1992, 1418-1419.