The multifaceted Diels-Alder reactivity of 4,6-dinitrobenzofuroxan and 4,6-dinitrobenzofurazan towards isoprene and 2,3-dimethylbutadiene

Arkivoc

Volumn 2004, Issue 3, 2004, Pages 85-100

  Goumont, Régis ^a   Sebban, Muriel ^a   Marrot, Jérome ^a   Terrier, François ^a  

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

Author keywords

Diels Alder Cycloadditions; Mono and di adducts; Nitrobenzofuroxans; Thermodynamic and kinetic control

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2,3 DIMETHYLBUTADIENE; 4,6 DINITROBENZOFURAZAN; 4,6 DINITROBENZOFUROXAN; BENZOFURAN DERIVATIVE; ISOPRENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COVALENT BOND; CYCLOADDITION; DIELS ALDER REACTION; NITROGEN NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 2942624155     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. (a) Terrier, F. In Nucleophilic Aromatic Displacement; Feuer, H, Ed.; VCH: New York, 1991;
2. (b) Terrier, F Chem. Rev. 1982, 82, 77;
3. (c) Buncel, E.; Dust, J. M.; Terrier, F Chem. Rev. 1995, 95, 2261.
4. (a) Terrier, F; Millot, F.; Norris, W. P. J. Am. Chem. Soc. 1976, 98, 5883 ;
5. (b) Terrier, F.; Chatrousse, A. P.; Soudais, Y; Hlaibi, M. J. Org. Chem. 1984, 49, 4176 ;
6. (c) Terrier, F.; Pouet, M. J.; Kizilian, E.; Hallé, J. C.; Outurquin, F.; Paulmier, C. J. Org. Chem. 1993, 58, 4696.
7. (a) Strauss, M. J.; Renfrow, R. A.; Buncel, E. J. Am. Chem. Soc. 1983, 105, 2473 ;
8. (b) Buncel, E.; Renfrow, R. A.; Strauss, M. J. J. Org. Chem. 1987, 52, 488;
9. (c) Buncel, E.; Dust, J. M.; Manderville, R. A. J. Am. Chem. Soc. 1996, 118, 6072;
10. (d) Buncel, E.; Manderville, R. A.; Dust, J. M. J. Chem. Soc. Perkin Trans 2. 1997, 1019 and references therein.
11. (a) Crampton, M. R.; Rabbitt, L. C. J. Chem. Soc. Perkin Trans 2. 1999, 1669;
12. (b) Crampton, M. R.; Rabbitt, L. C.; Terrier, F. Can. J. Chem. 1999, 77, 639;
13. (c) Crampton, M. R.; Rabbitt, L. C. J. Chem. Soc. Perkin Trans 2. 2000, 2159;
14. (d) Atherton, J. H.; Crampton, M. R.; Duffield, G. L.; Stevens, J. A. J. Chem. Soc. Perkin Trans 2. 1995, 443.
15. (a) Kind, J.; Niclas, H. J. Synth. Commun. 1993, 23, 1569;
16. (b) Niclas, H. J.; Göhrmann, B.; Gründemann Synth. Commun. 1989, 19, 2789.
17. Ghosh, P. B.; Ternai, B.; Whitehouse, M. W. Med. Res. Rev. 1981, 1, 159 and references therein.
18. Evgen'yev, M. I.; Garmonov, S. Y.; Evgen'yeva, M. I.; Gazizullina, L. S. J. Anal. Chem. 1998, 53, 57 and references therein.
19. Lowe-Ma, C. K.; Nissan, R. A.; Wilson, W. S. J. Org. Chem. 1990, 55, 3755.
20. Olekhnovich, L. P.; Budarina, Z. N.; Lesin, A. V.; Kurbatov, S. V.; Borodkin, G. S.; Minkin, V. I. Mendeleev Commun. 1994, 162.
21. (a) Terrier, F.; Kizilian, E.; Hallé, J. C.; Buncel, E. J. Am. Chem. Soc. 1992, 114, 1740;
22. (b) Kizilian, E.; Terrier, F.; Chatrousse, A. P.; Gzouli, K.; Hallé, J. C. J. Chem. Soc. Perkin Trans 2. 1997, 2567;
23. (c) Terrier, F.; Pouet, M. J.; Hallé, J. C.; Kizilian, E.; Buncel, E. J. Phys. Org. Chem. 1998, 11, 707;
24. (d) Terrier, F.; Pouet, M. J.; Gzouli, K.; Hallé, J. C.; Outurquin, F.; Paulmier, C. Can. J. Chem. 1998, 76, 937.
25. (a) Sebban, M.; Goumont, R.; Hallé, J. C.; Marrot, J.; Terrier, F. Chem. Commun. 1999, 1009 ;
26. (b) Terrier, F.; Sebban, M.; Goumont, R.; Hallé, J. C.; Moutiers, G.; Cangelosi, I. Buncel, E.; J. Org. Chem. 2000, 65, 7391 ;
27. (c) Sepulcri, P.; Goumont, R.; Hallé, J. C.; Riou, D.; Terrier, F. J. Chem. Soc. Perkin Trans. 2. 2000, 51 ;
28. (d) Goumont, R. ; Sebban, M. and Terrier, F. Chem. Commun., 2002, 2110.
29. Pugnaud, S.; Masure, D.; Hallé, J. C.; Chaquin, P. J. Org. Chem. 1997, 62, 8687.
30. Sepulcri, P.; Hallé, J. C.; Goumont, R.; Riou, D.; Terrier, F. J. Org. Chem. 1999, 64, 9254.
31. For the Diels-Alder reactivity of nitroalkenes, see : (a) Denmark, S. E., Thorarensen, A. Chem. Rev. 1996, 96, 137;
32. (b) Denmark, S. E., Hurd, S. R., Sacha, H. J. J. Org. Chem. 1997, 62, 1675;
33. (c) Denmark, S. E., Dixon, J. A. J. Org. Chem. 1998, 63, 6167, 6178.
34. (a) Hallé, J. C.; Vichard, D.; Pouet, M. J.; Terrier, F. J. Org. Chem. 1997, 62, 7178 ;
35. (b) Vichard, D.; Hallé, J. C.; Huguet, B.; Pouet, M. J.; Riou, D. ; Terrier, F. Chem. Commun. 1998, 791.
36. Goumont, R. ; Sebban, M. ; Sépulcri, P. ; Marrot, J. and Terrier, F. Tetrahedron, 2002, 58, 3249.
37. (a) Terrier, F.; Halle, J.C.; MacCormack, P.; Pouet, M. J.Can. J. Chem. 1988, 67, 503;
38. (b) MacCormack, P.; Halle, J.C.; Pouet, M.J.; Terrier, F. J. Org. Chem. 1988, 53, 4407.
39. Kresze, G.; Bathelt, H.; Tetrahedron 1973, 29, 1043.
40. Drost, P.; Liebigs Ann. Chem. 1899, 307, 49.
41. Read, R. W.; Spear, R. J.; Norris, W. P. Aust. J. Chem. 1983, 36, 1227.