Evidence for the intermediacy of Wheland-Meisenheimer complexes in S EAr reactions of aminothiazoles with 4,6-dinitrobenzofuroxan

Chemistry - A European Journal

Volumn 13, Issue 34, 2007, Pages 9600-9607

  Boga, Carla ^a   Del Vecchio, Erminia ^a   Forlani, Luciano ^a   Goumont, Régis ^b   Terrier, François ^b   Tozzi, Silvia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Aromatic substitution; Heterocycles; Reaction mechanisms; Reactive intermediates; Zwitterionic Wheland complexes

Indexed keywords

CHIRALITY; ETHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS;

AROMATIC SUBSTITUTION; HETEROCYCLES; REACTION MECHANISMS; REACTIVE INTERMEDIATES; ZWITTERIONIC WHELAND COMPLEXES;

AROMATIC COMPOUNDS;

EID: 36649003279     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700669     Document Type: Article

References (40)

1. a) L. Forlani, Targets Heterocyci Syst. 1997, 1, 75;
2. b) J. Elguero. C. Marzin, A. R. Katritzky. P. Linda, in The Tautomerism of Heterocycles, Academic Press, London, 1976.
3. a) L. Forlani, G. Breviglieri, P. De Maria, J. Chem. Soc. Perkin Trans. 2 1979, 163-165;
4. b) L. Forlani, P. De Maria, A. Fini, J. Chem. Soc. Perkin Trans. 2 1980, 1156-1158;
5. c) L. Forlani, P. De Maria, J. Chem. Soc. Perkin Trans. 2 1982, 535.
6. a) L. Forlani. P. De Maria, E. Foresti, G. Pradella, J. Org. Chem. 1981, 46, 3178-3181;
7. b) L. Forlani, M. Sintoni, J. Chem. Soc. Perkin Trans. 2 1988, 1959-1962.
8. a) L. Forlani. G. Guastadisegni, G. Raffellini, P. E. Todesco, E. Foresti, Gazz. Chim. Ital. 1990, 120, 493-499;
9. b) L. Forlani, L. P. Battaglia, A. Bonamartini Corradi, P. Sgarabotto. J. Cryst. Spectrosc. Res. 1992, 22, 705-712.
10. L. Forlani, M. Sintoni, P. E. Todesco, Gazz. Chim. Ital. 1986, 116, 229-232.
11. L. Forlani, J. Chem. Res. (S) 1990, 2, 70-71.
12. L. Forlani, A. L. Tocke, E. Del Vecchio, S. Lakhdar, R. Goumont, F. Terrier, J. Org. Chem. 2006, 71, 5527-5537.
13. C. Boga, E. Del Vecchio, L. Forlani, A. Mazzanti, P. E. Todesco, Angew. Chem. 2005, 117, 3349-3353;
14. Angew. Chem. Int. Ed. 2005, 44, 3285-3289.
15. F. Terrier, M. J. Pouet, K. Gzouli, J.-C. Hallé, F. Outurquin, C. Paulmier, Can. J. Chem. 1998. 76, 937-945.
16. a) E. Buncel, R. A. Renfrow, M. J. Strauss, J. Org. Chem. 1987, 52, 488-495:
17. b) F. Terrier, M. J. Pouet, J. C. Halle, E. Kizilian, E. Buncel, J. Phys. Org. Chem. 1998, 11, 707-714:
18. c) F. Terrier, M. J. Pouet, E. Kizilian, J. C. Halle, F. Outurquin. C. Paulmier, J. Org. Chem. 1993, 58, 4696-4702.
19. R. W. Read, R. J. Spear, W. P. Norris, Aust. J. Chem. 1984, 37, 985-999.
20. F. Terrier, in Nucleophilic Aromatic Displacement (Ed.: H. Feuer). VCH. New York, 1991, Chapter 2.
21. a) F. Terrier, F. Millot, W. P. Norris, J. Am. Chem. Soc. 1976, 98, 5883-5890;
22. b) S. Lakhdar, R. Goumont, T. Boubaker, M. Mokhtari, F. Terrier, Org. Biomol. Chem. 2006, 4, 1910-1919.
23. a) J. C. Hallé, M. J. Pouet, M. P. Simonin, F. Terrier, Tetrahedron Lett. 1985, 26, 1307;
24. b) F. Terrier, E. Kizilian, J. C. Hallé, E. Buncel, J. Am. Chem. Soc. 1992, 114, 1740-1742;
25. c) F. Terrier, M. J. Pouet, J. C. Hallé, S. Hunt, J. R. Jones, E. Buncel, J. Chem. Soc. Perkin Trans. 2 1993, 1665-1672.
26. E. Kizilian, F. Terrier, A. P. Chatrousse, K. Gzouli, J. C. Hallé. J. Chem. Soc. Perkin Trans. 2 1997, 2667-2672.
27. a) F. Terrier, S. Lakhdar, T. Boubaker, R. Goumont, J. Org. Chem. 2005, 70, 6242-6253;
28. b) S. Lakhdar, M. Westermaier, F. Terrier, R. Goumont, T. Boubaker, A. R. Ofial, H. Mayr, J. Org. Chem. 2006, 71, 9088-9095.
29. a) A. S. Bailey, J. R. Case, Tetrahedron 1958, 3, 113-131;
30. b) S. Sepulcri, R. Goumont, J. C. Hallé, E. Buncel. F. Terrier, Chem. Commun. 1997, 789-790.
31. We observed the formation of an N-σ adduct in the case of the reaction between DNBF and 2-amino-5-methylthiazole (27), in which position 5 cannot be reactive toward DNBF (see Experimental Section).
32. a) E. Buncel, M. R. Crampton, M.J. Strauss, F. Terrier, in Electron-Deficient Aromatic- and Heteroaromalic-Base Interactions, Elsevier. Amsterdam, 1984, Chapter 2;
33. b) M. R. Crampton, Adv. Phys. Org. Chem. 1969, 7, 211-257
34. c) M. J. Strauss. Chem. Rev. 1970, 70, 667-712.
35. L. Forlani. L. Lunazzi, A. Medici, Tetrahedron Lett. 1977, 18, 4525-4526.
36. L. Forlani, A. Medici, J. Chem. Soc. Perkin Trans. 1 1978, 10, 1169-1171.
37. R. Taylor, in Electrophilic Aromatic Substitutions, Wiley, New York, 1990.
38. F. Effenberger, Acc. Chem. Res. 1989, 22, 27-35.
39. S. Kurbatov, P. Rodriguez-Dafonte, R. Goumont, F. Terrier, Chem. Commun. 2003, 2150-2151.
40. S. Vogel, W. Knoche, W. W. Schoeller, J. Chem. Soc. Perkin Trans. 2 1986, 769-772.