Substituent effects on the lifetimes and reactivities of arylnitrenium ions studied by laser flash photolysis and photothermal beam deflection

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8127-8135

  Robbins, Rebecca J ^a   Laman, David M ^a   Falvey, Daniel E ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; IMINE;

ARTICLE; DRUG STABILITY; LASER; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0029787938     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961518z     Document Type: Article

References (66)

1. Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utilitv; 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. Frederick, C. B.; Beland, F. A. In Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships; Yang, S. K., Silverman, B. D., Eds.; CRC: Boca Raton, FL, 1988; Vol. II, pp 111-139.
4. Kadlubar, F. F. In DNA Adducts Identification and Significance; Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., Bartsch, H. Eds.; University Press: Oxford, UK, 1994; pp 199-216.
5. Kadlubar, F. F.; Beland, F. A. In Polycyclic Hydrocarbons and Carcinogens; Harvey, R. G., Ed.; American Chemical Society: Washington, DC, 1985.
6. Turesky, R. J.; Lang, N. P.; Butler, M. A.; Teitel, C. H.; Kadlubar, F. F. Carcinogenesis 1991, 12, 1839-1845.
7. Turesky, R.; Markovic, J. Chem. Res. Toxicol. 1994, 7, 752-761.
8. King, C. M.; Phillips, B. Science (Washington, DC) 1968, 159, 1351-1353.
9. Novak, M.; Roy, A. K. J. Org. Chem. 1985, 50, 571-580.
10. Novak, M.; Pelecanou, M.; Pollack, L. J. Am. Chem. Soc. 1986, 108, 112-120.
11. Bosold, F.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 63-64.
12. Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282.
13. Moore, P. D.; Rabkin, S. D.; Osborn, A.; King, C. M.; Strauss, B. S. Proc. Nail. Acad. Sci. U.S.A. 1982, 79, 7166-7170.
14. Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
15. Novak, M.; Kahley, M. J.; Eiger, E.; Helmick, J. S.; Peters, H. E. J. Am. Chem. Soc. 1993, 115, 9453-9460.
16. Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc: 1994, 116, 4513-4514.
17. Fishbein, J. C.; McClelland, R. A. J. Am. Chem. Soc. 1987, 109, 2824-2825.
18. Haley, N. F. J. Org. Chem. 1977, 42, 3929-3933.
19. Chiapperino, D.; Anderson, G. B.; Robbins, R. J.; Falvey, D. E. J. Org. Chem. 1996, 61, 3195-3199.
20. Anderson, G. B.; Yang, L. L.-N.; Falvey, D. E. J. Am. Chem. Soc. 1993, 115, 7254-7262.
21. Robbins, R. J.; Falvey, D. E. Tetrahedron Lett. 1994, 35, 4943-4946.
22. Robbins, R. J.; Yang, L. L.-N.; Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 6544-6552.
23. Peyerimhoff, S. D.; Buenker, R. J. Chem. Phys. 1979, 42, 167-176.
24. Gibson, S. T.; Greene, J. P.; Berkowitz, J. J. Chem. Phys. 1985, 83, 4319-4328.
25. Cramer, C. J.; Dulles, F. J.; Falvey, D. E. J. Am. Chem. Soc: 1994, 116, 9787-9788.
26. Li, Y.; Abramovitch, R. A.; Houk, K. N. J. Org. Chem. 1989, 54, 2911-2914.
27. Falvey, D. E.; Cramer, C. J. Tetrahedron Lett. 1992, 33, 1705-1708.
28. Ford, G. P.; Herman, P. S. J. Mol. Struct. (THEOCHEM) 1991, 236, 269-282.
29. Ford, G. P.; Herman, P. S. J. Am. Chem. Soc: 1989, 111, 3987-3996.
30. Glover, S. A.; Scott, A. P. Tetrahedron 1989, 45, 1763-1776.
31. Campbell, J. J.; Glover, S. A.; Rowbottom, C. A. Tetrahedron Lett. 1990, 37, 5377-5380.
32. Srivastava, S.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 10186-10193.
33. Ritchie, C. D. Can. J. Chem. 1986, 64, 2239-2259.
34. Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957.
35. Olah, G. A. Carbocations and Electrophilic Reactions: Wiley: New York, 1973; p 148.
36. Freedman, H. H. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1973; Vol. IV, pp 1501-1578.
37. Gassman, P. G.; Campbell, G. A. J. Am. Chem. Soc. 1971, 93, 2567-2569.
38. Gassman, P. G.; Campbell, G. A. J. Chem. Soc., Chem. Commun. 1970, 1970, 427.
39. Fishbein, J. C.; McClelland, R. A. J. Chem. Soc., Perkin Trans. 2 1995, 653-662.
40. Some nucleophiles do add to the nitrogen of nitrenium ions: most notably guanosine bases of DNA. For example, see ref 14.
41. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1994, 116, 11626-11627.
42. Mansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
43. McClelland, R. A.; Kanagasabapathy, V. M.; Banait, N. S.; Steenken, S. J. Am. Chem. Soc. 1991, 113, 1009-1014.
44. Stille, J. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
45. Kosugi, M.; Kato, Y.; Kiuchi, K.; Migita, T. Chem. Lett. 1981, 69-72.
46. Gassman, P. G.; Campbell, G. A.; Frederick, R. C. J. Am. Chem. Soc. 1972, 94, 3884-3891.
47. Gassman, P. G.; Campbell, G. A. J. Am. Chem. Soc. 1972, 94, 3891-3896.
48. Rosenthal, I. In Singlet Oxtgen; Frimel, A. H., Ed.; CRC Press: Boca Raton, FL, 1985: Vol. I, pp 13-35.
49. McClelland, R. A.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173-4174.
50. Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1993, 115, 9870-9871.
51. In contrast to the previously studied examples 2b, 2c, and 2d, the lifetimes of these longer-lived nitrenium ions are much more sensitive to traces of water in the solvent. The values cited would vary by ca. 10% from experiment to experiment.
52. Braslavsky, S. E.; Heibel, G. E. Chem. Rev. 1992, 92, 1381-1410.
53. Braslavsky, S. E.; Heinoff, K. In Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton. FL, 1989; Vol. 1, pp 327-355.
54. Tam, A. C.; Sontag, H.; Hess, P. Chem. Phys. Lett. 1985,120, 280-284.
55. Yeh, S.-R.; Falvey, D. E. J. Photochem. Photobiol. A: Chem. 1995, 87, 13-21.
56. Poston, P. E.; Harris, J. M. J. Photochem. Photobiol A: Chem. 1991, 60, 51-61.
57. Poston, P. E.; Harris, J. M. J. Am. Chem. Soc. 1990, 112, 644-650.
58. Laman, D. M.; Falvey, D. E. Rev. Sci. Instrum. 1996, (In Press).
59. Ginkel, F. I. M. v.; Visser, R. J.; Vanna, C. A. G. O.; Lodder, G. J. Photochem. 1985, 30, 453-473.
60. Johnston, L. J.; Schepp, N. P. J. Am. Chem. Soc. 1993, 115, 6564-6571.
61. Bartl, J.; Steenken, S.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 7710-7716.
62. Dorfman, L.; Sujdak, R. J.; Bockrath, B. Acc. Chem. Res. 1976, 9, 352-357.
63. Product studies showed a complex mixture of products when nitrenium ion 2f was generated in the presence of this nucleophile.
64. Steenken, S.; McClelland, R. A. J. Am. Chem. Soc. 1990, 112, 9648-9649.
65. Kobayashi, S.; Kitamura, T.; Taniguchi, H.; Schnabel, W. Chem. Lett. 1983, 1117-1120.
66. Bartl, J.; Steenken, S.; Mayr, H.; McClelland, R. A. J. Am. Chem. Soc. 1990, 112, 6918-6928.