Rate-limiting proton-transfer in the σ-adduct forming reactions of 1,3,5-trinitrobenzene and 4-nitrobenzofuroxan with substituted anilines in dimethyl sulfoxide

Organic and Biomolecular Chemistry

Volumn 3, Issue 21, 2005, Pages 3971-3978

  Asghar, Basim H M ^a   Crampton, Michael R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BENZENE; IONS; SULFUR COMPOUNDS;

ANILINES; DABCO; DIMETHYL SULFOXIDES; PROTON-TRANSFER;

PROTONS;

EID: 27844550719     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511644a     Document Type: Article

References (42)

1. For reviews, see: F. Terrier, Nucleophilic Aromatic Displacement, VCH, New York, 1991;
2. F. Terrier, Chem. Rev., 1982, 82, 77.
3. M. R. Crampton and V. Gold, J. Chem. Soc. B, 1967, 23.
4. C. F. Bernasconi, M. C. Muller and P. Schmid, J. Org. Chem., 1979, 44, 3189.
5. M. R. Crampton and B. Gibson, J. Chem. Soc., Perkin Trans. 2, 1981, 533.
6. M. R. Crampton and C. Greenhalgh, J. Chem. Soc., Perkin Trans. 2, 1983, 1175.
7. M. J. Kamlet and R. W. Taft, J. Am. Chem. Soc., 1976, 98, 377;
8. C. D. Ritchie and S. Lu, J. Am. Chem. Soc., 1989, 111, 8542.
9. M. R. Crampton, T. A. Emokpae, J. A. K. Howard, C. Isanbor and R. Mondai, Org. Biomol. Chem., 2003, 1, 1004.
10. M. R. Crampton and S. D. Lord, J. Chem. Soc., Perkin Trans. 2, 1997, 369.
11. M. R. Crampton, P. J. Routledge and P. Golding, J. Chem. Soc., Perkin Trans. 2, 1984, 329.
12. M. R. Crampton and P. J. Routledge, J. Chem. Soc., Perkin Trans. 2, 1984, 573.
13. M. R. Crampton and I. A. Robotham, J. Chem. Res. (S), 1997, 22.
14. E. Buncel and J. G. K. Webb, Can. J. Chem., 1972, 50, 129.
15. E. Buncel, H. Jarrell, H. W. Leung and J. G. K. Webb, J. Org. Chem., 1974, 39, 272.
16. E. Buncel and J. G. K. Webb, Can. J. Chem., 1974, 52, 630.
17. E. Buncel and H. W. Leung, J. Chem. Soc., Chem. Commun., 1975, 19.
18. E. Buncel and W. Eggimann, J. Am. Chem. Soc., 1977, 99, 5958.
19. E. Buncel, W. Eggimann and H. W. Leung, J. Chem. Soc., Chem. Commun., 1977, 55.
20. E. Buncel and W. Eggimann, J. Chem. Soc., Perkin Trans. 2, 1978, 673.
21. T. O. Bamkole, J. Hirst and I. Onyido, J. Chem. Soc., Perkin Trans. 2, 1981, 1201.
22. M. R. Crampton and I. Robotham, Can. J. Chem., 1998, 76, 627.
23. F. Terrier, F. Millot, A.-P. Chatrousse, M.-J. Pouet and M.-P. Simonnin, Org. Magn. Reson., 1976, 8, 56.
24. E. Buncel, N. Chuaqui-Offermanns, B. K. Hunter and A. R. Norris, Can. J. Chem., 1977, 55, 2852.
25. F. Terrier, A.-P. Chatrousse and F. Millot, J. Org. Chem., 1980, 45, 2666.
26. M. R. Crampton, L. M. Pearce and L. C. Rabbitt, J. Chem. Soc., Perkin Trans. 2, 2002, 257.
27. M. R. Crampton, J. Delaney and L. C. Rabbitt, J. Chem. Soc., Perkin Trans. 2, 1999, 2473.
28. C. Boga and L. Forlani, J. Chem. Soc., Perkin Trans. 2, 1998, 2155.
29. L. Forlani, M. Sintoni and P. E. Todesco, J. Chem. Res. (S), 1986, 344.
30. F. G. Bordwell, J. C. Branca, D. L. Hughes and W. N. Olmstead, J. Org. Chem., 1980, 45, 3305.
31. D. D. Perrin, Dissociation constants of organic bases in aqueous solution, Butterworths, London, 1972.
32. G. B. Barlin and D. P. Perrin, Q. Rev. Chem. Soc., 1966, 20, 75.
33. M. J. Kamlet and R. W. Taft, J. Am. Chem. Soc., 1976, 98, 377.
34. M. R. Crampton, J. Chem. Soc. B, 1971, 2112.
35. C. Boga and L. Forlani, J. Chem. Soc., Perkin Trans. 2, 2001, 1408.
36. C. F. Bernasconi, Pure Appl. Chem., 1982, 2335;
37. C. F. Bernasconi, Acc. Chem. Res., 1987, 20, 301;
38. C. F. Bernasconi, Adv. Phys. Org. Chem., 1992, 27, 119.
39. J.-C. Halle, M. Mokhtari, P. Soulie and M.-J. Pouet, Can. J. Chem., 1997, 75, 1240.
40. F. Terrier, M. Mokhtari, R. Goumont, J.-C. Halle and E. Buncel, Org. Biomol. Chem., 2003, 1, 1757.
41. F. G. Bordwell and A. H. Clemens, J. Org. Chem., 1981, 46, 1037;
42. F. G. Bordwell and D. L. Hugues, J. Am. Chem. Soc., 1986, 108, 5991.