Formation and reactivity of arylradicals from cathodic cleavage of halonitrobenzenes and related compounds

Electrochimica Acta

Volumn 43, Issue 21-22, 1998, Pages 3135-3140

  Pilard, Jean François ^a   Postec, Stéphanie ^a   Simonet, Jacques ^a   Mousset, Guy ^b  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Aryl radical and ESR spectroscopy; Electrochemical reduction; p halonitrobenzenes

Indexed keywords

ELECTROLYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; IONS; REDUCTION; SOLVENTS;

ARYL RADICAL; CATHODIC CLEAVAGE; DIMER RADICAL ANION; HALONITROBENZENE; ULTRAVIOLET VISIBLE SPECTROSCOPY;

ELECTROCHEMISTRY;

EID: 0032318821     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0013-4686(98)00071-1     Document Type: Article

References (28)

1. J. G. Lawless and M. D. Hawley, J. Electroanal. Chem. 21, 365 (1969).
2. G. R. Compton, R. A. W. Dryfe and A. C. Fisher, J. Electroanal. Chem. 361, 275 (1993).
3. V. D. Parker, Acta Chem. Scand. B 35(9), 655 (1981).
4. G. R. Compton, R. A. W. Dryfe and A. C. Fisher, J. Chem. Soc. Perkin Trans. 2, 1581 (1994).
5. G. R. Compton and R. A. W. Dryfe, J. Electroanal. Chem. 375, 247 (1994).
6. W. C. Danen, T. T. Kensler, J. G. Lawless, M. F. Marcus and M. D. Hawley, J. Phys. Chem. 73(12), 4389 (1969).
7. H. Balslev and H. Lund, Tetrahedron 50(26), 7889 (1994).
8. F. Ammar and J. M. Savéant, J. Electroanal. Chem. 47, 115 (1973).
9. D. Wipf and M. Wightman, J. Phys. Chem. 93, 4286 (1989).
10. C. Galli, Tetrahedron 44(16), 5205 (1988).
11. N. Alam, C. Amatore, C. Combellas, J. Pinson, J. M. Savéant, A. Thiébault and J. N. Verpeaux, J. Org. Chem. 53, 1496 (1988).
12. X. M. Zhang, D. L. Yang, X. Q. Jia and Y. C. Liu, J. Org. Chem. 58, 7350 (1993).
13. R. Rossi and S. M. Palacios, Tetrahedron 49(21), 4485 (1993).
14. J. Robert, M. Anouti, G. Bosser, J. L. Parrain and J. Paris, J. Chem. Soc. Perkin Trans. 2, 1639 (1995).
15. G. Bosser, M. Benaïchouche, R. Coudert and J. Paris, New J. Chem. 18, 511 (1994).
16. J. R. Beck, Tetrahedron 34, 2057 (1978).
17. E. G. Janzen, Acc. Chem. Res. 4, 31 (1971).
18. A. J. Bard, J. C. Gilbert and R. D. Goodin, J. Am. Chem. Soc. 96(2), 620 (1974).
19. E. G. Janzen, G. A. Coulter, U. M. Oehler and J. P. Bergsna, Can. J. Chem. 60, 2725 (1982).
20. R. H. Cox, E. G. Janzen and J. L. Gerlock, J. Am. Chem. Soc. 90(21), 5909 (1968).
21. Electrogenerated free radicals could be trapped either by nitrosoindurene or PBN. see for example: (a) P. Martigny, J. Simonet, G, Mousset and J. Vigneron, N. J. Chim., 1983, 7, 299; (b) R. Kossai, B. Emir, J. Simonet and G. Mousset, J. Electroanal. Chem., 1989, 270, 253.
22. Electrogenerated free radicals could be trapped either by nitrosoindurene or PBN. see for example: (a) P. Martigny, J. Simonet, G, Mousset and J. Vigneron, N. J. Chim., 1983, 7, 299; (b) R. Kossai, B. Emir, J. Simonet and G. Mousset, J. Electroanal. Chem., 1989, 270, 253.
23. E. G. Janzen, E. R. Davis and C. M. Dubose, Magnet. Res. Chem. 33, 5166 (1995).
24. R. F. Bridger and G. A. Russel, J. Am. Chem. Soc. 85(4), 3754 (1963).
25. C. Amatore, J. Pinson, J. M. Savéant and A. Thiébault, J. Am. Chem. Soc. 104, 817 (1982).
26. A. Sauer, F. Wasgestian and U. Nickel, Bull. Chem. Soc. Jpn. 62, 2688 (1989).
27. M. Brenda, A. Knebelkamp, A. Greiner and W. Heitz, Synlett, 809, (1991).
28. J. Rault-Berthelot, V. Questaigne and J. Simonet, New J. Chem. 13, 45 (1989).