Two-photon laser-induced reaction of 1,8-bis(halomethyl)naphthalenes from different excited states and transient targeting of its intermediate by time-delayed, two-color photolysis and argon ion laser-jet photolysis techniques

Journal of the American Chemical Society

Volumn 119, Issue 3, 1997, Pages 592-599

  Ouchi, Akihiko ^a   Koga, Yoshinori ^a   Adam, Waldemar ^b  

^a NATL INST OF MAT AND CHEM RES   (Japan)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; LASER; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0031028850     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962884l     Document Type: Article

References (45)

1. (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58.
2. (b) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249.
3. (c) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
4. (d) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558.
5. (e) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum. 1991, 4, 8-17.
6. (a) Wilson, R. M.; Hannemann, K.; Peters, K.; Peters, E.-M. J. Am. Chem. Soc. 1987, 109, 4741-4743.
7. (b) Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. 1989, 30, 6851-6854.
8. (c) Bendig, J.; Mitzner, R. Ber. Bunsen-Ges. Phys. Chem. 1994, 98, 1004-1008.
9. (d) Mathews, M. G.; Wang, Z.; Koplitz, B. Chem. Phys. Lett. 1994, 227, 633-638.
10. Preliminary results: (a) Ouchi, A.; Yabe, A. Tetrahedron Lett. 1992, 33, 5359-5362. (b) Adam, W.; Ouchi, A. Tetrahedron Lett. 1992, 33, 1875-1878. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946.
11. Preliminary results: (a) Ouchi, A.; Yabe, A. Tetrahedron Lett. 1992, 33, 5359-5362. (b) Adam, W.; Ouchi, A. Tetrahedron Lett. 1992, 33, 1875-1878. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946.
12. Preliminary results: (a) Ouchi, A.; Yabe, A. Tetrahedron Lett. 1992, 33, 5359-5362. (b) Adam, W.; Ouchi, A. Tetrahedron Lett. 1992, 33, 1875-1878. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946.
13. (a) Slocum, G. H.; Kaufman, K.; Schuster, G. B. J. Am. Chem. Soc. 1981, 103, 4625-4627.
14. (b) Kelley, D. F.; Milton, S. V.; Huppert, D.; Rentzepis, P. M. J. Phys. Chem. 1983, 87, 1842-1843.
15. (c) Gould, I. R.; Tung, C.; Turro, N. J.; Givens, R. S.; Matuszewski, B. J. Am. Chem. Soc. 1984, 106, 1789-1793.
16. (d) Hilinski, E. F.; Huppert, D.; Kelley, D. F.; Milton, S. V.; Rentzepis, P. M. J. Am. Chem. Soc. 1984, 106, 1951-1957.
17. (e) Slocum, G. H.; Schuster, G. B. J. Org. Chem. 1984, 49, 2177-2185.
18. (f) Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1985, 107, 6368-6372.
19. (g) Tolumura, K.; Udagawa, M.; Itoh, M. J. Phys. Chem. 1985, 89, 5147-5149.
20. (h) Arnold, B.; Donald, L.; Jurgens, A.; Pincock, J. A. Can. J. Chem. 1985, 63, 3140-3146.
21. (i) Scaiano, J. C.; Johnston, L. J. Pure Appl. Chem. 1986, 58, 1273-1278.
22. (j) van Haelst, L.; Haselbach, E.; Suppan, P. Chimia 1988, 42, 231-234.
23. (k) Redmond, R. W.; Wayner, D. D. M.; Kanabus-Kaminska, J. M.; Scaianao, J. C. J. Phys. Chem. 1989, 93, 6397-6401.
24. (l) Kawai, A.; Okutsu, T.; Obi, K. Chem. Phys. Lett. 1990, 174, 213-218.
25. (m) Kawai, A.; Okutsu, Y.; Obi, K. Chem. Phys. Lett. 1995, 235, 450-455.
26. (a) Gisin, M.; Wirz, J. Helv. Chim. Acta 1976, 59, 2273-2277.
27. (b) Pagni, R. M.; Burnett, M. N.; Dodd, J. R. J. Am. Chem. Soc. 1977, 99, 1972-1973.
28. (c) Platz, M. S. J. Am. Chem. Soc. 1979, 101, 3398-3399.
29. (d) Platz, M. S. J. Am. Chem. Soc. 1980, 102, 1192-1194.
30. (e) Platz, M. S.; Carrol, G.; Pierrat, F.; Zayas, J.; Auster, S. Tetrahedron 1982, 38, 777-785.
31. (f) Haider, K.; Platz, M. S.; Despres, A.; Lejenne, V.; Migirdicyan, E.; Bally, T.; Haselbach, E. J. Am. Chem. Soc. 1988, 110, 2318-2320.
32. (g) Biewer, M. C.; Platz, M. S.; Roth, M.; Wirz, J. J. Am. Chem. Soc. 1991, 113, 8069-8073.
33. The experimental results are given as Supporting Information.
34. Ito, O.; Alam, M. M.; Koga, Y.; Ouchi, A. J. Photochem. Photobiol., A 1996, 97, 19-23.
35. The effect of other halogen atom scavengers was also studied and the results are given as Supporting Information.
36. (a) Calvert, J. G.; Pitts, J. G., Jr. Photochemistry; John Wiley & Sons: New York, 1966; Chapter 5, Section 5-8.
37. (b) Horspool, W.; Armesto, D. Organic Photochemistry; Ellis Horwood PTR Prentice Hall: Chichester, 1992; Chapter 6, Section 6.1.
38. Huppert, D.; Rand, S. D.; Reynolds, A. H.; Rentzepis, P. M. J. Chem. Phys. 1982, 77, 1214-1224.
39. Carmichael, I.; Hug, G. L. Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, 1989; Vol. I, Chapter 16.
40. 6
41. 17 Therefore, the escape of halogen atoms will be larger in acetonitrile than in cyclohexane so that the higher consumption of 1 and the yield of 4 should be observed.
42. In addition to a radical reaction path, the presence of an ionic path has been reported in the photolysis of 5 in methanol: ref 4e.
43. Preparation of compounds la,b is given as Supporting Information.
44. Leffler, J. E. An introduction to free radicals; John Wiley & Sons: New York, 1993; Chapter 4, Section 4.2.2.
45. Riddick, J. A.; Bunger, W. B. Techniques of Chemistry, Organic Solvents, 3rd ed.; Wiley-Interscience Publication, John Wiley & Sons: New York, 1970; pp 139 and 399.