Spectroscopy and kinetics of triplet 4-methylbenzenesulfonylnitrene

Journal of Physical Chemistry

Volumn 100, Issue 14, 1996, Pages 5788-5793

  Garay, Jean Claude ^a   Maloney, Vincent ^a   Marlow, Matthew ^a   Small, Phillip ^a  

^a INDIANA UNIVERSITY PURDUE UNIVERSITY FORT WAYNE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS; PARAMAGNETIC RESONANCE; PHOTOCHEMICAL REACTIONS; SPECTROSCOPIC ANALYSIS; SULFUR COMPOUNDS;

EPR SPECTRUM; LASER FLASH PHOTOLYSIS; TRIPLET METHYLBENZENESULFONYLNITRENE;

NITROGEN COMPOUNDS;

EID: 0030568438     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9528525     Document Type: Article

References (53)

1. Schuster, G. B.; Platz, M. S. In Advances in Photochemistry, Volman, D., Hammond, G., Neckers, D. Eds.; John Wiley & Sons: New York, 1992; Vol. 17.
2. Platz, M. S.; Maloney V. M. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990; Chapter 8 and references therein.
3. Platz, M. S. In Azides and Nitrenes; Academic Press: Orlando, FL, 1984; Chapter 7 and references therein.
4. Thrush, B. A. Proc. R. Soc. London, Ser. A 1956, 253, 143.
5. Reviews of laser flash photolysis studies of carbenes can be found in ref 2 and in: Moss, R. A.; Turro, T. J. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; Chapter 7.
6. Scriven, E. F. V., Ed. Azides and Nitrenes; Academic Press: Orlando, FL, 1984.
7. Lwowski, W., Ed. Nitrenes; Wiley Interscience: New York, 1970.
8. Liang, T.-Y.; Schuster, G. B. J. Am. Chem. Soc. 1987, 109, 7803.
9. Kobayashi, T.; Ohtani, H.; Suzuki, K.; Yamaoka, T. J. Phys. Chem. 1985, 89, 776.
10. Houser, M.; Kelley, S.; Maloney, V.; Marlow, M.; Steininger, K.; Zhou, H. J. Phys. Chem. 1995, 99, 7946.
11. (a) Breslow, R.; Herman, F.; Schwabacher, A. W. J. Am. Chem. Soc. 1984, 106, 5359.
12. (b) Breslow, R.; Feiring, A.; Herman, F. J. Am. Chem. Soc. 1974, 96, 5937.
13. (a) Maslak, P.; Sczepanski, J. J.; Minard, R. D.; Collins, L. A. Tetrahedron Lett. 1990, 31, 4261.
14. (b) Maslak, P. J. Am. Chem. Soc. 1989, 111, 8201.
15. Lwowski, W. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: Orlando, FL, 1984; Chapter 4.
16. Jackson, James E., Michigan State University. Personal communication.
17. (a) Moss, R. A.; Feydorynski, M.; Shieh, W.-C. J. Am. Chem. Soc. 1979, 101, 4738.
18. (b) Atkinson, R. S.; Martin, R. J. Chem. Soc., Chem. Commun. 1974, 386.
19. (a) Breslow, D. S. In Nitrenes; Lwowski, W., Ed.; Wiley Interscience: New York, 1970; Chapter 8 and references therein.
20. (b) Abramovitch, R. A.; Davis, B. A. Chem. Rev. 1964, 149 and references therein.
21. (a) Smolinsky, G.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1962, 84, 3320.
22. (b) Moriarty, R. M.; Rahman, M.; King, G. J. J. Am. Chem. Soc. 1966, 88, 842.
23. (c) Wasserman, E. Prog. Phys. Org. Chem. 1971, 8, 319.
24. Reference 13, p 226.
25. Reagan, M. T.; Nickon, A. J. Am. Chem. Soc. 1968, 90, 4096.
26. Reichle, W. T. Inorg. Chem. 1964, 3, 402.
27. (a) Lwowski, W.; Scheiffele, E. J. Am. Chem. Soc. 1965, 87, 4359.
28. (b) Lwowski, W.; De Mauriac, R.; Mattingly, T. W., Jr.; Scheiffele, E. Tetrahedron Lett. 1964, 3285.
29. Horner, L.; Christmann, A. Chem. Ber. 1963, 96, 388.
30. (a) Breslow, D. S.; Sloan, M. F.; Newburg, N. R.; Renfrew, W. B. J. Am. Chem. Soc. 1969, 91, 2273.
31. (b) Sloan, M. F.; Renfrew, W. B.; Breslow, D. S. Tetrahedron Lett. 1964, 2905.
32. (a) Leffler, J. E.; Tsuno, Y. J. Org. Chem. 1963, 28, 190.
33. (b) Leffler, J. E.; Tsuno, Y. J. Org. Chem. 1963, 28, 902.
34. (a) In the case of fluorenylidene, it is more convenient to monitor to growth of the fluorenyl radical upon hydrogen abstraction by triplet fluorenylidene than the triplet carbene itself.
35. (b) Griller, D.; Montgomery, C. R.; Scaiano, J. C. ; Platz, M. S.; Hadel, L. M. J. Am. Chem. Soc. 1982, 104, 6813.
36. (c) Brauer, B.-E.; Grasse, P. B.; Kaufmann, K. J.; Schuster, G. B. J. Am. Chem. Soc. 1982, 104, 6814.
37. (d) Grasse, P. B.; Brauer, B.-E.; Zupancic, J. J.; Kaufmann, K. J.; Schuster, G. B. J. Am. Chem. Soc. 1983, 105, 6833.
38. (e) Griller, D.; Hadel, L. M.; Nazran, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227.
39. Savino, T. G.; Senthilnathan, V. P.; Platz, M. S. Tetrahedron 1986, 42, 2167.
40. Poe, R.; Grayzar, J.; Young, M. J. T.; Leyva, E.; Schnapp, K. A.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 3209.
41. Schnapp, K. A.; Platz, M. S. Bioconjugate Chem. 1993, 4, 178.
42. (a) McClelland, R. A.; Davidse, P. A., Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173.
43. (b) Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513.
44. Leyva, E.; Platz, M. S.; Niu, B.; Wirz, J. J. Phys. Chem. 1987, 91, 2293.
45. Hansch, Leo; Taft, R. W. Chem. Rev. 1991, 91, 165.
46. Murov, S. L. Handbook of Photochemistry; Marcel Dekker: New York, 1973; p 89.
47. (a) Brinen, J. S.; Singh, B. J. Am. Chem. Soc. 1971, 93, 6623.
48. (b) Abramovitch, R. A.; Challand, R. S. J. Chem. Soc., Chem. Commun. 1972, 964.
49. (c) Go, C. L.; Waddell, W. H. J. Org. Chem. 1983, 48, 2897.
50. (d) Sawaki, Y.; Ishikawa, S.; Iwamura, H. J. Am. Chem. Soc. 1987, 109, 584.
51. (a) Bohme, P.; Hicke, H.-G.; Boettcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 5824.
52. (b) Harmer, M. A. Langmuir 1991, 7, 2010.
53. (c) Holden, D. A.; McGarvey, C. E. Langmuir 1990, 6, 1123.