Anodic Coupling of Diphenylbenzo[k]fluoranthene: Mechanistic and Kinetic Studies Utilizing Cyclic Voltammetry and Electrogenerated Chemiluminescence

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 530-537

  Debad, Jeff D ^a   Morris, Jonathan C ^a   Magnus, Philip ^a   Bard, Allen J ^a  

^a The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002022792     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961448e     Document Type: Article

References (34)

1. (a) McKillop, A.; Turell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504.
2. (b) Eberson, L.; Hartshorn, M. P.; Persson, O. J. Chem. Soc., Perkins Trans. 2 1995, 409.
3. See, for example: (a) Yoshida, K. Electrooxidation in Organic Chemistry. The Role of Cation Radicals as Synthetic Intermediates; John Wiley and Sons: New York, 1984. (b) Shono, T. Electroorganic Synthesis; Academic Press: London, 1991. (c) Kyriacou, D. Modern Electroorganic Chemistry; Springer-Verlag: Berlin, 1994.
4. See, for example: (a) Yoshida, K. Electrooxidation in Organic Chemistry. The Role of Cation Radicals as Synthetic Intermediates; John Wiley and Sons: New York, 1984. (b) Shono, T. Electroorganic Synthesis; Academic Press: London, 1991. (c) Kyriacou, D. Modern Electroorganic Chemistry; Springer-Verlag: Berlin, 1994.
5. See, for example: (a) Yoshida, K. Electrooxidation in Organic Chemistry. The Role of Cation Radicals as Synthetic Intermediates; John Wiley and Sons: New York, 1984. (b) Shono, T. Electroorganic Synthesis; Academic Press: London, 1991. (c) Kyriacou, D. Modern Electroorganic Chemistry; Springer-Verlag: Berlin, 1994.
6. For reviews on ECL see: (a) Knight, A. W.; Greenway, G. M. Analyst 1994, 119, 879. (b) Faulkner, L. R.; Bard, A. J. In Electroanalytical Chemistry; Marcel Dekker: New York, 1977; Vol. 10, p 1.
7. For reviews on ECL see: (a) Knight, A. W.; Greenway, G. M. Analyst 1994, 119, 879. (b) Faulkner, L. R.; Bard, A. J. In Electroanalytical Chemistry; Marcel Dekker: New York, 1977; Vol. 10, p 1.
8. Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374.
9. Eaton, D. F. Pure Appl. Chem. 1988, 60, 1107.
10. Morris, J. V.; Mahaney, M. A.; Huber, J. R. J. Phys. Chem. 1976, 80, 969.
11. McCord, P.; Bard, A. J. J. Electroanal. Chem. 1991, 318, 91.
12. Denuault, G.; Mirkin, M. V.; Bard, A. J. J. Electroanal. Chem. 1991, 308, 27.
13. Mitchell, R. H.; Chaudhary, M.; Williams, R. V.; Flyes, R.; Gibson, J.; Ashwood-Smith, M. J.; Fry, A. J. Can. J. Chem. 1992, 70, 1015.
14. Plummer, B. F.; Steffan, L. K.; Braley, T. L.; Reese, W. G.; Zych, K.; Van Dyke, G.; Tulley, B. J. Am. Chem. Soc. 1993, 115, 11542.
15. See the Experimental Section for details on the preparation and characterization of this compound.
16. Fanta, P. E. Synthesis 1974, 9.
17. Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627 and references therein.
18. (a) Peover, M. E. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1967; Vol. 2, p 1.
19. (b) VolSaji, T.; Aoyagui, S. J. Electroanal. Chem. 1983, 144, 143.
20. (c) Jensen, B. S.; Parker, V. D. J. Am. Chem. Soc. 1975, 97, 5211.
21. (d) Saji, T.; Aoyagui, S. J. Electroanal. Chem. 1979, 98, 163.
22. (e) Chang, J.; Hercules, D. M.; Roe, D. K. Electrochim. Acta 1968, 13, 1197.
23. (f) Bard, A. J. Pure Appl. Chem. 1971, 25, 379.
24. (a) Werner, T. C.; Chang, J.; Hercules, D. M. J. Am. Chem. Soc. 1970, 92, 5560.
25. (b) Fleet, B.; Keliher, P. N.; Kirkbright, G. F.; Pickford, C. J. Analyst 1969, 94, 847.
26. (c) Werner, T. C.; Chang, J.; Hercules, D. M. J. Am. Chem. Soc. 1970, 92, 763.
27. Bard, A. J.; Faulkner, L. R. Electrochemical Methods; John Wiley and Sons: New York, 1980.
28. Yang, H.; Wipf, D. O.; Bard, A. J. J. Electroanal. Chem. 1992, 331, 913.
29. For example, see: (a) Larumbe, D.; Gallardo, I.; Andrieux, C. P. J. Electroanal. Chem. 1991, 304, 241. (b) Yang, H.; Bard, A. J. J. Electroanal. Chem. 1991, 306, 87. (c) Marcoux, L. S.; Adams, R. N.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2611. (d) Nelson, R. F.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2623.
30. For example, see: (a) Larumbe, D.; Gallardo, I.; Andrieux, C. P. J. Electroanal. Chem. 1991, 304, 241. (b) Yang, H.; Bard, A. J. J. Electroanal. Chem. 1991, 306, 87. (c) Marcoux, L. S.; Adams, R. N.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2611. (d) Nelson, R. F.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2623.
31. For example, see: (a) Larumbe, D.; Gallardo, I.; Andrieux, C. P. J. Electroanal. Chem. 1991, 304, 241. (b) Yang, H.; Bard, A. J. J. Electroanal. Chem. 1991, 306, 87. (c) Marcoux, L. S.; Adams, R. N.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2611. (d) Nelson, R. F.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2623.
32. For example, see: (a) Larumbe, D.; Gallardo, I.; Andrieux, C. P. J. Electroanal. Chem. 1991, 304, 241. (b) Yang, H.; Bard, A. J. J. Electroanal. Chem. 1991, 306, 87. (c) Marcoux, L. S.; Adams, R. N.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2611. (d) Nelson, R. F.; Feldberg, S. W. J. Phys. Chem. 1969, 73, 2623.
33. Andrieux, C. P.; Savéant, J. M. In Investigations of Rate and Mechanisms of Reactions Part II; Bernasconi, C. F., Ed.; John Wiley and Sons: New York, 1986; Chapter VII.
34. Nadjo, L.; Savéant, J. M. J. Electroanal. Chem. 1973, 44, 327.