Reactivity of singlet and triplet arylnitrenes: Temperature-dependent photodecomposition of 1-(2-azidophenyl)-3,5-dimethylpyrazole

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7308-7315

  Albini, Angelo ^a   Bettinetti, Gianfranco ^a   Minoli, Giovanna ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZOLE DERIVATIVE;

ARTICLE; IN VITRO STUDY; PHOTOCHEMISTRY; PHOTODEGRADATION; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0030852244     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970588i     Document Type: Article

References (33)

1. (a) Schuster, G. B.; Platz, M. S. Adv. Photochem. 1992, 17, 69.
2. (b) Platz, M. S.; Leyva, E.; Haider, K. Org. Photochem. 1991, 11, 367.
3. (c) Platz, M. S. Acc. Chem. Res. 1995, 28, 487 and references cited.
4. (a) Li, Y. Z.; Kirby, J. P.; George, M. W.; Poliakoff, M.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 8092.
5. (b) Schrock, A. K.; Schuster, G. B. J. Am. Chem. Soc. 1984, 106, 5228.
6. (c) Li, Y. Z.; Kirby, J. P.; George, M. W.; Poliakoff, M.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 8092.
7. Meijer, E. W. Nijhuis, S.; Von Vroonhoven, F. C. B. M. J. Am. Chem. Soc. 1988, 110, 7209.
8. Leyva, E.; Platz, M. S.; Persy, G.; Wirz, J. J. Am. Chem. Soc. 1986, 108, 3783.
9. Marcinek, A.; Leyva, E.; Whitt, D.; Platz, M. S. J. Am. Chem. Soc. 1993, 115, 8609.
10. Reiser, A.; Bowes, G.; Horne, R. J. Trans. Faraday Soc. 1966, 62, 3162.
11. Hayes, J. C.; Sheridan, R. S. J. Am. Chem. Soc. 1990, 112, 5879.
12. (a) Chapman, O. L.; Le Roux, J. P. J. Am. Chem. Soc. 1978, 100, 282.
13. (b) Chapman, O. L. Sheridan, R. S. J. Am. Chem. Soc. 1979, 101, 3690.
14. (c) Dunkin, I. R.; Donelly, T.; Lockhart, T. S. Tetrahedron Lett. 1985, 359.
15. (d) Donnelly, T., Dunkin, I. R.; Norwood, D. S. D.; Prentice, A.; Shields, C. J.; Thompson, P. C. P. J. Chem. Soc., Perkin Trans. 2 1985, 2147.
16. (a) Liang, T. Y.; Schuster, G. B. J. Am. Chem. Soc. 1987, 109, 7804.
17. (b) Odum, R. A.; Aaronson, A. M. J. Am. Chem. Soc. 1969, 91, 5680.
18. Lindley, J. M.; McRobbie, I. M.; Meth-Cohn, O.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1 1980, 982.
19. Albini, A.; Bettinetti, G.; Minoli, G. Chem. Lett. 1981, 301.
20. Albini, A.; Bettinetti, G.; Minoli, G. Heterocycl. 1995, 597.
21. Albini, A.; Bettinetti, G.; Minoli, G. J. Org. Chem. 1983, 48, 1080. Albini, A.; Bettinetti, G.; Minoli, G. J. Chem. Soc., Perkin Trans. 1 1983, 581.
22. Albini, A.; Bettinetti, G.; Minoli, G. J. Org. Chem. 1983, 48, 1080. Albini, A.; Bettinetti, G.; Minoli, G. J. Chem. Soc., Perkin Trans. 1 1983, 581.
23. Kim, S. J.; Hamilton, T. P.; Schaefer, H. F. J. Am. Chem. Soc. 1992, 114, 5349.
24. (a) Crystallographic analysis on azide 5 shows that the pyrazole is tilted out of the phenyl ring plane; two independent molecules in the cell, torsion angles 65.77 and 83.30°, respectively (B. Bovio, Pavia, personal communication). Molecular model calculation reproduce a similar result both from the azide and the nitrene. (b) The glassy solution softens at a relatively low temperature (95 K for MP and 120 K for EtOH). This makes the observed product distribution significant for the irradiation temperature, since the intermediates are directly converted to the final products in the experiments at these temperatures or immediately upon softening of the glass for the few experiments below them.
25. (6) Hayes, R.; Schofield, J. M.; Smalley, R. C.; Scopes, D. I. C. Tetrahedron 1990, 46, 2089.
26. (b) Albini, A.; Bettinetti, G.; Minoli, G. J. Org. Chem. 1991, 56, 6993.
27. Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc. 1991, 113, 6928.
28. (a) Hrovat, D. A.; Waali, E. E.; Borden, W. T. J. Am. Chem. Soc. 1992, 114, 8698.
29. (b) Travers, M. J.; Cowles, D. C.; Clifford, E. P.; Ellison, G. B. J. Am. Chem. Soc. 1992, 114, 8699.
30. (c) Drzaic, P. S.; Brauman, J. I. J. Phys. Chem. 1984, 88, 5285.
31. (d) Drzaic, P. S.; Brauman, J. I. J. Am. Chem. Soc. 1984, 106, 3443.
32. Abramovitch, R. A.; Challand, S. R. J. Chem. Soc., Chem. Commun. 1972, 964.
33. Bettinetti, G. F.; Fasani, E.; Minoli, G.; Pietra, S. Gazz. Chim. Ital. 1979, 109, 175.