Photogenerated diarylnitrenium ions: Laser flash photolysis and product studies on diphenylnitrenium ion generated from photolysis of 1-(N,N-diphenylamino)pyridinium ions

Journal of the American Chemical Society

Volumn 118, Issue 37, 1996, Pages 8965-8966

  Moran, Ricardo J ^a   Falvey, Daniel E ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; LASER; PHOTOCHEMISTRY; PHOTOLYSIS;

EID: 0029830739     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961086s     Document Type: Article

References (37)

1. Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, FL, 1984: pp 297-357.
2. Simonova, T. P.; Nefedov, V. D.; Toropova, M. A.: Kirillov, N. F. Russ. Chem. Rev 1992, 61, 584-599.
3. Heller, H. E.; Hughes, E. D.; Ingold, C. K. Nature 1951, 168, 909-910.
4. Davidse, P. A. Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116,4513-4514.
5. Srivastava, S.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 10186-10193.
6. McClelland, R. A.; Kahley, M. J.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1996, 118, 4794-4803.
7. McClelland, R. A.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173-4174.
8. Certain highly stabilized diarylnitrenium ions have been detected as intermediates in the electrochemical oxidation of substituted diarylamine. For example: Serve, D. J. Am. Chem. Soc. 1975, 97, 432-434.
9. Eisenthal, K. B.; Turro, N. J.; Sitzmann, E. V.; Gould, I. R.; Hefferon, G.; Langan, J.; Cha, Y. Tetrahedron 1985, 41, 1543-1545.
10. Schuster, G. B. Adv. Phys. Org. Chem. 1986, 22, 311-361.
11. Platz, M. S.; Maloney, V. M. In Kinetics and Spectroscopy of Carbenes and Biradicals: M. S. Platz, Ed.; Plenum: New York, 1990; pp 239-352.
12. Dorfman, L.; Sujdak, R. J.; Bockrath, B, Acc. Chem. Res. 1976, 9, 352-357.
13. Belt, S. T.; Bohne, C.; Charette, G.; Sugamori, S. E.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 2200-2205.
14. Bartl, J.; Steenken, S.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 7710-7716.
15. Anderson, G. B.; Yang, L. L.-N.; Falvey, D. E. J. Am. Chem. Soc. 1993, 115, 7254-7262.
16. Abramovitch, R. A.; Shi, Q. Heterocycles 1994, 37, 1463-1466.
17. Takeuchi, H.; Hayakawa, S.; Tanahashi, T.; Kobayashi, A.; Adachi, T.; Higuchi, D. J. Chem. Soc., Perkin Trans. 2 1991, 847-855.
18. Abramovitch, R. A.; Becken, J. M.; Chinnasamy, P.; Xiaohua, H.; Pennington, W.; Sanjivamurthy, A. R. V. Heterocyles 1989, 28, 623-628.
19. Gassman, P. G.; Campbell, G. A. J. Am. Chem. Soc. 1972, 94, 3891-3896.
20. Novak, M.; Pelecanou, M.; Roy, A. K.; Andronico, A. F.; Plourde, F.; Olefirowicz, T. M.; Curtin, T. J. J. Am. Chem. Soc. 1984, 106, 5623-5631.
21. Gassman, P. G.; Campbell, G. A.; Frederick, R. C. J. Am. Chem. Soc. 1972, 94, 3884-3891.
22. Fishbein, J. C.; McClelland, R. A. J. Chem. Soc. Perkin Trans. 2 1995, 663-671.
23. •, which also has a broad absorption in this region. The singlet nitrenium ion signal at 425 nm is not noticeably affected by the acid. A more complete analysis of this issue will he presented in the full paper.
24. Weir, D.; Scaiano, J. C.; Schuster, D. I. Can, J. Chem. 1988, 66, 2595-2600.
25. Scheerer, R.; Grätzel, M. J. Am. Chem. Soc. 1977, 99, 865-871.
26. Shida, T.; Hamill, W. H. J. Chem. Phys. 1966, 44, 2369-2374.
27. Mayr, H.; Patz, M. Angew, Chem., Int. Ed. Engl. 1994, 33, 938-957.
28. Robbins, R. J.; Yang, L. L.-N.; Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 6544-6552.
29. Rosenthal, I. In Singlet Oxygen; Frimel, A. H., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. I, pp 13-35.
30. Griller, D.; Nazran, A. S.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 198-202.
31. Cramer, C. J.; Dulles, F. J.; Falvey, D. E. J. Am. Chem. Soc. 1994, 116, 9787-9788.
32. Li, Y.; Abramovitch, R. A.; Houk, K. N. J. Org. Chem. 1989, 54, 2911-2914.
33. Ford, G. P., Scribner, J. D. J. Am. Chem. Soc. 1981, 103, 4281-4291.
34. Ford, G. P.; Herman, P. S. J. Mol. Stuct. (THEOCHEM) 1991, 236, 269-282.
35. Ullman, E. F.; Singh, P. J. Am. Chem. Soc. 1972, 94, 5077-5078.
36. Abramovitch, R. A.; Evertz, K.; Huttner, G.; Gibson, H. H.; Weems, H. G. J. Chem. Soc. Chem. Commun. 1988, 325-327.
37. Takeuchi, H.; Higuchi, D.; Adachi, T. J. Chem. Soc. Perkin Trans. 2 1991, 1525-1529.