New reactivity patterns in the Diels-Alder reactivity of nitrobenzofuroxans

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 2000, Pages 51-54

  Sepulcri, Patricia ^a   Goumont, Régis ^a   Hallé, Jean Claude ^a   Riou, Didier ^a   Terrier, François ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYST SELECTIVITY; CONDENSATION; ELECTRONS; HYDROGEN BONDS; MOLECULAR STRUCTURE; REACTION KINETICS; THERMODYNAMIC STABILITY; X RAY ANALYSIS;

DIELS ALDER REACTIVITY; NITROBENZOFUROZANS; REACTIVITY PATTERNS; REGIOSELECTIVE; STEREOSELECTIVE;

NITROGEN COMPOUNDS;

EID: 0033993066     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907552f     Document Type: Article

References (51)

1. (a) F. Terrier, in Nucleophilic Aromatic Displacement; The Influence of the Nitro Group, Organic Nitro Chem. Ser., ed. H. Feuer, VCH, New York, 1991 chapters 1 and 2
2. (b) E. Buncel, J. M. Dust and F. Terrier, Chem. Rev., 1995, 95, 2261
3. (c) F. Terrier, Chem. Rev., 1982, 82, 77.
4. (a) F. Terrier, F. Millot and W. P. Norris, J. Am. Chem. Soc., 1976, 98, 5883
5. (b) F. Terrier, M. J. Pouet, E. Kizilian, J. C. Hallé, F. Outurquin and C. Paulmier, J. Org. Chem., 1993, 58, 4696
6. (c) F. Terrier, E. Kizilian, J. C. Hallé and E. Buncel, J. Am. Chem. Soc., 1992, 114, 1740 and references therein.
7. (a) M. J. Strauss, R. A. Renfrow and E. Buncel, J. Am. Chem. Soc., 1983, 105, 2473
8. (b) E. Buncel, R. A. Renfrow and M. J. Strauss, J. Org. Chem., 1987, 52, 488
9. (c) E. Buncel, R. A. Manderville and J. M. Dust, J. Chem. Soc., Perkin Trans. 2, 1997, 1019 and references therein.
10. (a) R. J. Spear, W. P. Norris and R. W. Read, Tetrahedron Lett., 1983, 24, 1555
11. (b) W. P. Norris, R. J. Spear and R. W. Read, Aust. J. Chem., 1983, 36, 297.
12. (a) J. Kind and H. J. Niclas, Synth. Commun., 1993, 23, 1569
13. (b) H. J. Niclas and B. Göhrmann, Synth. Commun., 1989, 19, 2141
14. (c) H. J. Niclas, B. Göhrmann and E. Gründemann, Synth. Commun., 1989, 19, 2789.
15. (a) P. B. Ghosh, B. Ternai and M. W. Whitehouse, Med. Res. Rev., 1981, 1, 159
16. (b) P. B. Ghosh and M. W. Whitehouse, J. Med. Chem., 1968, 11, 305
17. (c) P. B. Ghosh and M. W. Whitehouse, J. Med. Chem., 1969, 12, 505
18. (d) P. B. Ghosh and B. J. Everitt, J. Med. Chem., 1974, 17, 203.
19. M. I. Evgen'yev, S. Y. Garmonov, I. I. Evgen'yeva and L. S. Gazizullina, J. Anal. Chem., 1998, 53, 571 and references therein.
20. C. K. Lowe-Ma, R. A. Nissan and W. S. Wilson, J. Org. Chem., 1990, 55, 3755.
21. (a) E. Kizilian, F. Terrier, A. P. Chatrousse, K. Gzouli and J. C. Hallé, J. Chem. Soc., Perkin Trans. 2, 1997, 2667
22. (b) F. Terrier, M. J. Pouet, J. C. Hallé E. Kizilian and E. Buncel, J. Phys. Org. Chem., 1998, 11, 707
23. (c) F. Terrier, M. J. Pouet, K. Gzouli, J. C. Hallé, F. Outurquin and C. Paulmier, Can. J. Chem., 1998, 76, 937.
24. (a) J. H. Atherton, M. R. Crampton, G. L. Duffield and J. A. Stevens, J. Chem. Soc., Perkin Trans. 2, 1995, 443
25. (b) M. R. Crampton and L. C. Rabbit, J. Chem. Soc., Perkin Trans. 2, 1999, 1669.
26. G. Kresze and H. Bathelt, Tetrahedron, 1973, 29, 1043.
27. (a) J. C. Hallé, D. Vichard, M. J. Pouet and F. Terrier, J. Org. Chem., 1997, 62, 7178
28. (b) D. Vichard, J. C. Hallé, B. Huguet, M. J. Pouet, D. Riou and F. Terrier, Chem. Commun., 1998, 791
29. (c) P. Sepulcri, R. Goumont, J. C. Hallé, D. Riou and F. Terrier, J. Org. Chem., 1999, 64, 0000.
30. S. Pugnaud, D. Masure, J. C. Hallé, and P. Chaquin, J. Org. Chem., 1997, 62, 8687.
31. S. Weinreb and D. B. Boger, in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, Orlando, 1987.
32. (a) S. E. Denmark, B. S. Kesler and Y. C. Moon, J. Org. Chem., 1992, 57, 4912
33. (b) S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137 and references therein
34. (c) S. E. Denmark and A. Thorarensen, J. Am. Chem. Soc., 1997, 119, 127
35. (d) S. E. Denmark, R. A. Hurd and H. J. Sacha, J. Org. Chem., 1997, 62, 1668
36. (e) S. E. Denmark and L. R. Marcin, J. Org. Chem., 1997, 62, 1675.
37. W. A. Sheppard, J. Am. Chem. Soc., 1963, 85, 1314.
38. F. G. Bordwell, N. R. Vanier, W. S. Matthews, J. B. Hendrickson and P. L. Skipper, J. Am. Chem. Soc., 1975, 97, 7160.
39. F. Terrier, F. Millot and J. Morel, J. Org. Chem., 1976, 41, 3892.
40. (a) L. M. Yagupol'skii, A. Ya. Ll'chenko and N. V. Kondratenko, Russ. Chem. Rev., 1974, 43, 32
41. (b) J. M. Carpentier, F. Terrier, R. Schaal, N. V. Ignatev, V. N. Boiko and L. M. Yagupol'skii, Bull. Soc. Chim. Fr., 1985, 150.
42. F. Terrier, E. Kizilian, R. Goumont, N. Faucher and C. Wakselman, J. Am. Chem. Soc., 1998, 120, 9496.
43. G. Raabe, H. J. Gais and J. Fleischhauer, J. Am. Chem. Soc., 1996, 118, 4622.
44. B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York, 1994, 81.
45. (a) A. Ejchart, Org. Magn. Reson., 1977, 10, 263
46. (b) F. Terrier, R. Goumont, M. J. Pouet and J. C. Hallé, J. Chem. Soc., Perkin Trans. 2, 1995, 1629.
47. P. Sepulcri, Ph.D. Thesis, University of Versailles, March 1999.
48. L. M. Yagupol'skii, I. V. Gogoman, G. M. Shchupak and V. N. Boiko, Zh. Org. Khim., 1986, 22, 743.
49. B. Ghosh, B. Ternai and M. W. Whitehouse, J. Med. Chem., 1972, 15, 255.
50. G. Sheldrick, SADABS program, Siemens Area Detector Absorption Corrections, unpublished.
51. SHELXTL: Structure Analysis Program 5.04; Siemens Industrial Automation, Inc., Madison, WI, 1995.