Carbon-halogen bond cleavage energies of polyhaloalkyl radical anions in solution

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1457-1460

  Cheng, Jin Pei ^a   Zheng, Zirong ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGENATED HYDROCARBON;

ARTICLE; DRUG STRUCTURE; ELECTROCHEMISTRY; ENTHALPY;

EID: 0029965833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00040-8     Document Type: Article

References (32)

1. (a) Russell, G. A. Advances in Physical Organic Chemistry; Bethell, D., Ed.; Vol. 23, 271-322, Academic: London, 1987.
2. (b) Bard, A. J. and Lund, H. Encyclopedia of Electrochemistry of the Elements; Marcel Dekker: New York, Vol. XIV, 1980.
3. Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
4. (a) Parker, V. D. Acta Chem. Scand. 1992, 46, 307.
5. (b) Zhang, X.-M. J. Chem. Soc. Perkin Trans. 2 1993, 2275.
6. (c) Daasbjerg, K. ibid 1994, 1275.
7. (a) Bordwell, F. G.; Bausch, M. J. J. Amer. Chem. Soc. 1986, 108, 2473.
8. (b) Bordwell, F. G.; Cheng, J.-P.; Bausch, M. J. ibid. 1988, 110, 2867, 2872.
9. (c) Bordwell, F. G.; Cheng, J.-P.; Seyedrezai, S. E.; Wilson, C. A. ibid 1988, 110, 8178.
10. (d) Bordwell, F. G.; Cheng, J.-P. ibid 1989, 111, 1792.
11. (e) Zhao, Y.; Huan, Z.-W.; Cheng, J.-P. Chem. J. Chin. Univ. 1994, 15, 207.
12. Nicholas, A. M. De P.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165.
13. (a) Cheng, J.-P.; Handoo, K. L.; Parker, V. D. J. Amer. Chem. Soc. 1993, 115, 2655.
14. (b) Handoo, K. L. ; Cheng, J.-P.; Parker, V. D. ibid 1993, 115, 5067.
15. (c) Cheng, J.-P.; Handoo, K. L.; Parker, V. D. J. Org. Chem. 1993, 58, 5050.
16. (a) Bordwell, F. G.; Cheng, J.-P.; Harrelson, J. A., Jr. J. Amer. Chem. Soc. 1988, 110, 1229.
17. (b) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. ibid 1991, 113, 9790.
18. (c) Parker, V. D. ibid 1992, 114, 7458.
19. (d) Bordwell, F. G.; Zhang, X.-M. Acc. Chem. Res. 1993, 26, 510.
20. (e) Arnett, E. M.; Amarnath, K.; Harvey, N. G.; Cheng, J.-P. J. Amer. Chem. Soc. 1990, 112, 344.
21. (a) Zhao, Y.; Cheng, J. P. Tetrahedron 1993, 49, 5267.
22. (b) Zhao, Y.; Huan, Z.-W.; Cheng, J. P. Acta Chimica Sinica 1994, 52, 980.
23. (c) Cheng, J.-P.; Zhao, Y.; Huan, Z.-W. Science in China (Series B) 1995, 25, 804.
24. (d) Cheng, J.-P.; Liu, B.; Li, Z.; Huan, Z.-W. Chin. Sci. Bull. 1995, 40, 1338.
25. Experimental conditions for electrochemical measurements were the same as previously described in reference 8(a).
26. RX/RX-., due to an increase in stability of the radical anions by multi-halogen substitution. We thank one referee for pointing out this difference.
27. Symons, M. C. R.; Smith, I. G. J. Chem. Soc. Faraday Trans, 1 1985, 81, 1095.
28. (a) Andrieux, C. P.; Savéant, J.-M.; Su, K. B. J. Phys. Chem. 1986, 90, 3815.
29. (b) Andrieux, C. P.; Hapiot, P.; Savéant, J.-M. Chem. Rev. 1990, 90, 723 and references therein.
30. Calculated according to reference 14.
31. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applicatons; Wiley: New York, 1980.
32. Breslow, R.; Chu. W. J. Amer. Chem. Soc. 1973, 95, 410.