Titanium dioxide photocatalyzed oxygenation of naphthalene and some of its derivatives

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 2000, Pages 699-704

  Soana, Federica ^a   Sturini, Michela ^a   Cermenati, Laura ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; MASS SPECTROMETRY; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; OXIDATION; PHOTOCATALYSIS; POLYCYCLIC AROMATIC HYDROCARBONS;

FORMYLCINNAMALDEHYDES; HYDROXY GROUPS; NAPHTHOLS; NAPHTHOQUINONE; OZONATION; PHOTOCATALYZED OXYGENATION;

TITANIUM DIOXIDE;

EID: 0034175159     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908945d     Document Type: Article

References (54)

1. (a) A. Mills and S. Le Hunte, J. Photochem. Photobiol., A: Chem., 1997, 108, 1
2. (b) P. Pichat, in Handbook of Heterogeneous Catalysis, eds. G. Ertl, H. Knoezinger and J. Weitkamp, Wiley, New York, 1997, p. 2111
3. (c) D. Bahnemann, J. Cunningham, M. A. Fox, E. Pelizzetti, P. Pichat and N. Serpone, in Aquatic and Surface Photochemistry, eds. G. R. Helz, R. G. Zepp and D. G. Crosby, Lewis Pub., Boca Raton, 1994, p. 261
4. (d) M. R. Hoffmann, S. T. Martin, W. Choi and D. W. Bahnemann, Chem. Rev., 1993, 93, 671
5. (e) O. Legrini, E. Oliveros and A. M. Braun, Chem. Rev., 1993, 93, 671
6. (f) P. Pichat, Catal. Today, 1994, 19, 313
7. (g) P. Pichat, C. Guillard, C. Maillard, L. Amalric and J. C. D'Oliveira, in Photocatalytic Purification and Treatment of Water and Air, Elsevier, Amsterdam, 1993, p. 207
8. (h) N. Serpone, E. Pelizzetti and H. Hidaka, in ref. (g), p. 225
9. (i) R. W. Matthews, in ref. (g), p. 121
10. (j) M. A. Fox, in ref. (g), p. 163.
11. (a) M. A. Fox, Top. Curr. Chem., 1987, 142, 71
12. (b) M. A. Fox and M. T. Dulay, Chem. Rev., 1993, 93, 341
13. (c) H. Kisch, J. Prakt. Chem., 1994, 336, 635
14. (d) E. Baciocchi, C. Rol, G. V. Sebastiani and L. Taglieri, J. Org. Chem., 1994, 59, 5272
15. (e) R. Kuenneth, C. Feldmer, F. Knoch and H. Kisch, Chem. Eur. J., 1995, 1, 441
16. (f) W. Schindler, F. Knoch and H. Kisch, Chem. Ber., 1996, 129, 925
17. (g) L. Cermenati, M. Mella and A. Albini, Tetrahedron, 1998, 54, 2575.
18. (a) K. A. Gray and U. Stafford, Res. Chem. Intermed., 1994, 20, 835
19. (b) L. Amalric, C. Guillard and P. Pichat, Res. Chem. Intermed., 1994, 20, 579
20. (c) J. Schwitzgebel, J. G. Ekerdt, H. Gerischer and A. Heller, J. Phys. Chem., 1995, 99, 5633
21. (d) Y. Sun and J. Pignatello, J. Environ. Sci. Technol., 1995, 29, 2065
22. (e) P. PIchat, L. Cermenati, A. Albini, D. Mas, H. Delprat and C. Guillard, Res. Chem. Intermed., 2000, 26, 161.
23. N. Serpone, D. Lawless, R. Khairutdinov and E. Pelizzetti, J. Phys. Chem., 1993, 90, 16655.
24. (a) L. Cermenati, P. Pichat, C. Guillard and A. Albini, J. Phys. Chem., B, 1997, 101, 2650
25. (b) L. Cermenati, A. Albini, P. Pichat and C. Guillard, Res. Chem. Intermed., 2000, in press.
26. S. Das, M. Muneer and K. R. Gopidas, J. Photochem. Photobiol., A: Chem., 1994, 77, 83
27. (b) C. Guillard, H. Delprat, C. Hoang-Van and P. Pichat, J. Atm. Chem., 1993, 16, 47
28. (c) J. Theurich, D. W. Bahnemann, R. Vogel, F. E. Ehamed, G. Alhakimi and I. Rajab, Res. Chem. Intermed., 1997, 23, 247
29. (d) J. C. Ireland, B. Davila, H. Moreno, S. K. Fink and S. Tassos, Chemosphere, 1995, 30, 965
30. (e) J. Kiwi, C. Pulgarin, P. Peringer and M. Graetzel, New J. Chem., 1993, 17, 487
31. (f) P. Foster, V. Jacob, M. Laffond and R. Perraud, in Physico-Chemical Behaviour of Atmospheric Pollutants, eds. G. Restelli and G. Angeletti, Kluwer, Dordrecht, 1990, p. 289
32. (g) R. W. Matthews, in Photochemical Conversion and Storage of Solar Energy, eds. E. Pelizzetti and M. Schiavello, Kluwer, Dordrecht, 1990, p. 427.
33. M. A. Fox, C. C. Chen and J. N. Younathan, J. Org. Chem., 1984, 49, 1969.
34. (a) A. Heller, Acc. Chem. Res., 1995, 28, 503
35. (b) A. Sobczynski, L. Duczmal and A. Dobosz, Monatsh. Chem., 1999, 130, 377.
36. R. A. Larson, W. J. Garrison and K. A. Marley, Tetrahedron Lett., 1986, 34, 3987.
37. Y. I. Pyatnitskii, Russ. Chem. Rev., 1976, 45, 762.
38. F. Freeman, in Organic Synthesis by Oxidation with Metal Compounds, eds. W. J. Mijs and C. R. H. I. de Jonge, Plenum Press, New York, 1986, p. 1.
39. P. S. Bailey, Ozonation in Organic Chemistry, Academic Press, London, 1982, p. 46.
40. M. Doré, Chimie des Oxydants et Traitments des Eaux, Lavoisier, Paris, 1989.
41. (a) P. S. Bailey, S. S. Bath, F. Dobison, J. F. Garcia-Sharp and C. D. Johnson, J. Org. Chem., 1964, 29, 697
42. (b) P. S. Bailey and F. J. Garcia-Sharp, J. Org. Chem., 1957, 22, 1008
43. (c) C. D. Johnson and P. S. Bailey, J. Org. Chem., 1964, 29, 703.
44. (a) B. H. J. Bielski, Photochem. Photobiol., 1978, 28, 645
45. (b) C. von Sonntag, The Chemical Basis of Radiation Biology, Taylor & Francis, London, 1987
46. (c) Z. B. Alfassi (ed.), Peroxyl Radicals, Wiley, Chichester, 1997
47. (d) C. Walling, Acc. Chem. Res., 1998, 31, 155
48. (e) J. A. Howard, Isr. J. Chem., 1984, 24, 33
49. (f) G. Ghigo and G. Tonachini, J. Am. Chem. Soc., 1999, 121, 8366.
50. M. Schäfer-Ridder, U. Bracke and E. Vogel, Angew. Chem., Int. Ed. Engl., 1976, 15, 228.
51. N. Darby, T. M. Cresp and F. Sondheimer, J. Org. Chem., 1977, 42, 1960.
52. Y. Kuroda, A. Kunai, M. Hamada, T. Kitano, S. Ito and K. Sasaki, Bull. Chem. Soc. Jpn., 1991, 64, 3089.
53. C. Richard, New J. Chem., 1994, 18, 443.
54. M. A. Fox and C.C. Chen, J. Am. Chem. Soc., 1981, 103, 6757.