New insights on N-tert-butyl-α-phenylnitrone (PBN) as a spin trap. Part 1. Reaction between PBN and N-chlorobenzotriazole

Journal of the Chemical Society. Perkin Transactions 2

Volumn 7, Issue , 1996, Pages 1297-1305

  Carloni, Patricia ^a   Eberson, Lennart ^b   Greci, Lucedio ^a   Sgarabotto, Paolo ^c   Stipa, Pierluigi ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b LUND UNIVERSITY   (Sweden)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010776320     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960001297     Document Type: Article

References (47)

1. (a) P. Carloni, L. Eberson, L. Greci, P. Stipa and G. Tosi, J. Chem. Soc., Perkin Trans. 2, 1991, 1779;
2. (b) R. Andruzzi, C. Berti, L. Greci and A. Trazza, J. Org. Chem., 1982, 47, 4895.
3. (a) E. G. Janzen, Acc. Chem. Res., 1971, 4, 31;
4. (b) M. J. Perkins, Adv. Phys. Org. Chem., 1980, 17, 1;
5. (c) V. Zubarev and O. Brede, J. Chem. Soc., Perkin Trans. 2, 1994, 1821.
6. L. Eberson, M. P. Hartshorn and O. Persson, J. Chem. Soc., Perkin Trans. 2, 1996, 141.
7. L. Eberson, J. Lind and G. Merenyi, J. Chem. Soc., Perkin Trans. 2, 1994, 1181.
8. L. B. Volodarsky, Imidazoline Nitroxides, CRC Press, Inc., Boca Raton, Florida, 1988, vol. 1, p. 175.
9. (a) A. Escande, J. L. Galign and J. Lapasset, Acta Crystallogr., Sect. B, 1974, 30, 1490;
10. (b) R. Bosch, G. Jung and W. Winter, Acta Crystallogr., Sect. C, 1983, 39, 1089;
11. (c) A. R. Katritzky, J. Wu, L. Wrobel, S. Rachwal and P. J. Steel, Acta Chem. Scand., 1993, 47, 167.
12. L. Pauling, The Nature of the Chemical Bond, 3rd edn., Cornell University Press, Ithaca, 1960, pp. 232-240.
13. H. J. Bernstein, Trans. Faraday Soc., 1961, 57, 1649.
14. (a) M. Iwamura and N. Inamoto, Bull. Chem. Soc. Jpn., 1967, 40, 702;
15. (b) M. Iwamura and N. Inamoto, Bull. Chem. Soc. Jpn., 1970, 43, 856;
16. (c) O. W. Maender and E. G. Janzen, J. Org. Chem., 1969, 34, 4072.
17. (a) H. G. Aurich, S. K. Duggal, P. Hohlein, H.-G. Klingelhofer and W. Weiss, Chem. Ber., 1981, 114, 2440;
18. (b) E. G. Janzen and B. J. Blackburn, J. Am. Chem. Soc., 1969, 91, 4481;
19. (c) M. Colonna, L. Greci and L. Marchetti, Tetrahedron, 1975, 31, 1745.
20. N-Chlorobenzotriazole may be the most important oxidant present in solution suitable for this oxidation.
21. L. Eberson, J. Chem. Soc., Perkin Trans. 2, 1992, 1807.
22. M. J. Davies, B. C. Gilbert, J. K. Stell and A. C. Whitwood, J. Chem. Soc., Perkin Trans. 2, 1992, 333.
23. L. Eberson, J. E. Barry, M. Finkelstein, W. M. Moore and S. D. Ross, Acta Chem. Scand., Ser. B, 1986, 40, 283.
24. M. S. Ram and D. M. Stanbury, Inorg. Chem., 1995, 24, 4234.
25. J. Lind, X. Shen, T. E. Eriksen, G. Merenyi and L. Eberson, J. Am. Chem. Soc., 1991, 113, 4629;
26. J. Lind, M. Jonsson, T. E. Eriksen, G. Merenyi and L. Eberson, J. Phys. Chem., 1993, 97, 1610.
27. (a) K. V. Lichman, J. Chem. Soc. C, 1971, 2539;
28. (b) P. M. Bowyer, D. H. Iles and A. Ledwith, J. Chem. Soc. C, 1971, 2775;
29. (c) M. Cinquini and S. Colonna, Synthesis, 1972, 259.
30. (a) C. W. Rees and R. C. Storr, J. Chem. Soc. C, 1969, 1474;
31. (b) W. D. Kingsbury and C. R. Johnson, J. Chem. Soc., Chem. Commun., 1969, 65.
32. G. L. McIntire, H. N. Blount, H. J. Stronks, R. V. Shetty and E. G. Janzen, J. Phys Chem., 1980, 84, 916.
33. For calculation of the electrostatic term, see: L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer-Verlag, Heidelberg, 1987.
34. P. Carloni, L. Eberson L. Greci and P. Stipa, unpublished results.
35. (a) L. Eberson, M. P. Hartshorn, F. Radner and O. Persson, J. Chem. Soc., Chem. Commun., 1996, 215;
36. (b) L. Eberson, M. P. Hartshorn, F. Radner and O. Persson, in Res. Chem. Intermed., 1996, in the press;
37. L. Eberson, M. P. Hartshorn and O. Persson, Angew. Chem., 1995, 107, 2417.
38. M. Ogata, H. Kano and K. Tori, Chem. Pharm. Bull., 1963, 11, 1527.
39. E. G. Janzen, G. Chen, T. M. Bray, L. A. Reinke, J. L. Poyer and P. B. McCay, J. Chem. Soc., Perkin Trans. 2, 1993, 1983.
40. C. W. Rees and R. C. Storr, J. Chem. Soc., Chem. Commun., 1968, 1305.
41. L. Eberson and L. Jonsson, Acta Chem. Scand., Ser. B, 1986, 40, 79.
42. G. A. Russel, E. G. Janzen and E. T. Strom, J. Am. Chem. Soc., 1964, 86, 1806.
43. G. M. Sheldrick, SHELXS86, Program for the Solution of Crystal Structures, University of Göttingen, 1986.
44. G. M. Sheldrick, SHELX76, System of Computer Programs for Crystal Structure Determination, University of Cambridge, 1976.
45. M. Nardelli, Comput. Chem., 1983, 7, 95.
46. M. S. Lehmann and F. K. Larsen, Acta Crystallogr., Sect. A, 1974, 30, 580.
47. International Tables for X-Ray Crystallography, Kynoch Press, Birmingam, 1974, vol. IV.