Wallach rearrangement of azoxypyridines and azoxypyridine N-oxides - Charge distributions and dramatic reactivity differences

Canadian Journal of Chemistry

Volumn 86, Issue 4, 2008, Pages 298-304

  Buncel, Erwin ^a   Keum, Sam Rok ^a,c   Rajagopal, Srinivasan ^a   Kiepek, Eric ^a   Cox, Robin A ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b Department of New Mat Chem ^*  (Canada)

^c Korea University   (South Korea)

Author keywords

Azoxypyridine N oxides; Azoxypyridines; Basicities; Charge distributions; Excess acidity; Reactivities; Theoretical calculations; Wallach rearrangement

Indexed keywords

CHARGE DISTRIBUTION; ISOMERS; SULFURIC ACID;

AZOXYPYRIDINES; EXCESS ACIDITY; THEORETICAL CALCULATIONS; WALLACH REARRANGEMENT;

AROMATIC COMPOUNDS;

EID: 42149147953     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V08-016     Document Type: Article

References (37)

1. O. Wallach and E. Belli. Chem. Ber. 13, 525 (1880).
2. E. Buncel and B.T. Lawton. Chem. Ind. (London), 1835 (1963).
3. E. Buncel and B.T. Lawton. Can. J. Chem. 43, 862 (1965).
4. E. Buncel, W.M.J. Strachan, R.J. Gillespie, and R. Kapoor. J. Chem. Soc., Chem., Commun. 765 (1969).
5. E. Buncel and W.M.J. Strachan. Can. J. Chem. 48, 377 (1970).
6. R.A. Cox. J. Am. Chem. Soc. 96, 1059 (1974).
7. R.A. Cox, D.Y.K. Fung, I.G. Csizmadia, and E. Buncel. Can. J. Chem. 81, 535 (2003).
8. (a) E. Buncel and A. Dolenko. Tetrahedron Lett. 113 (1971);
9. (b) A. Dolenko and E. Buncel. Can. J. Chem. 52, 623 (1974);
10. (c) E. Buncel, R.A. Cox, and A. Dolenko. Tetrahedron Lett. 215 (1975);
11. (d) R.A. Cox, A.J. Dolenko, and E. Buncel. J. Chem. Soc., Perkin Trans. 2, 471 (1975).
12. (a) R.A. Cox and E. Buncel. J. Chem. Soc, Chem. Commun. 1259 (1972);
13. (b) E. Buncel and R.A. Cox. Can. J. Chem. 51, 3143 (1973);
14. (c) R.A. Cox and E. Buncel. J. Am. Chem. Soc. 97, 1871 (1975).
15. E. Buncel and S.-R. Keum. J. Chem. Soc., Chem. Commun. 578 (1983).
16. E. Buncel, A. Dolenko, I.G. Csizmadia, J. Pincock and K. Yates. Tetrahedron, 24, 6671 (1968).
17. E. Buncel, S.-R. Keum, M. Cygler, K.I. Varughese, and G.I. Birnbaum. Can. J. Chem. 62, 1628 (1984).
18. E.V. Brown, and G.R. Granneman. J. Am. Chem. Soc. 97, 621 (1975).
19. G.M. Badger and G.E. Lewis. J. Chem. Soc. 2151 (1953).
20. (a) M. Colonna, A. Risaliti, and L. Pentimalli. Gazz. Chem. Ital. 86, 1067 (1956);
21. (b) M. Colonna and A. Risaliti. Gazz. Chim. Ital. 85, 1148 (1955).
22. L. Pentimalli. Ann. Chim. (Rome), 55, 435 (1965).
23. R.J. Gillespie and S. Wasif. J. Chem. Soc. 213 (1953).
24. R.A. Cox. Adv. Phys. Org. Chem. 35, 1 (2000).
25. R.A. Cox and K. Yates. J. Am. Chem. Soc. 100, 3861 (1978).
26. R.A. Cox. Can. J. Chem. 83, 1391 (2005).
27. R.A. Cox and K. Yates. Can. J. Chem. 59, 1560 (1981).
28. E. Buncel and J.M. Dust. Carbanion chemistry. Structures and mechanisms. American Chemical Society, WA, and Oxford University Press, Oxford, UK. 2003.
29. (a) E. Buncel. In Mechanisms of molecular migrations. Vol. 1. Edited by B.S. Thyagarajan. Wiley, New York. pp. 61-119. 1968;
30. (b) E. Buncel. Acc Chem. Res. 8, 132 (1975);
31. (c) R.A. Cox and E. Buncel. In The chemistry of the hydrazo, azo, and azoxy groups. Vol. 1. Edited by S. Patai. Wiley, London, pp. 775-859. 1975;
32. (d) R.A. Cox and E. Buncel. In The chemistry of the hydrazo, azo, and azoxy groups. Vol. 2. Edited by S. Patai. Wiley, London. 1997. pp. 569-602;
33. (e) D. Abdallah, M.A.A. Ghani, M.F. Cunningham, P.M. Kazmaier, B. Keoshkerian, and E. Buncel. Can. J. Chem. 82, 1393 (2004).
34. R.A. Cox. Can. J. Chem. 86, this issue.
35. (a) Y. Zhang, D.J. DeSchepper, T.M. Gilbert, K.K.S. Sai, and D.A. Klumpp. J. Chem. Soc., Chem. Commun. 4032 (2007);
36. (b) S. Saito, Y. Sato, T. Ohwada, and K. Shudo. J. Am. Chem. Soc. 116, 2312 (1994);
37. (c) T. Ohwada, T. Ohta, and K. Shudo. J. Am. Chem. Soc. 108, 3029 (1986).