Effect of high pressure on Michael and Henry reactions between ketones and nitroalkanes

New Journal of Chemistry

Volumn 23, Issue 5, 1999, Pages 525-529

  Jenner, Gérard ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; CHLOROFORM; KETONE DERIVATIVE; NITROALKANE; NITROMETHANE; TETRAHYDROFURAN; WATER;

ARTICLE; CALCULATION; CHEMICAL REACTION; HYPERBARISM; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032766249     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900899c     Document Type: Article

References (30)

1. G. Rosini and R. Ballini, Synthesis, 1988, 833.
2. J. Boyer, R. Corriu, R. Perz and C. Reye, Tetrahedron, 1983, 39, 117.
3. Y. Nishigaichi, A. Takuwa, Y. Naruta and K. Maruyama, Tetrahedron, 1993, 49, 7395.
4. A. Lubineau and J. Augé, Tetrahedron Lett., 1992, 33, 8073.
5. Rosini, in Comprehensive Organic Chemistry, eds. B. Trost and C. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, p. 322.
6. As a recent example: R. Chinchilla, C. Nagera and P. Sanchez-Agullo, Tetrahedron: Asymmetry, 1994, 5, 1393.
7. R. Ballini and G. Bosica, J. Org. Chem., 1997, 62, 425.
8. (a) G. Jones, Org. React., 1967, 15, 254.
9. (b) A. T. Nielsen, Org. React., 1968, 16, 1.
10. (a) K. Matsumoto, Angew. Chem., Int. Ed. Engl., 1980, 19, 1013.
11. (b) K. Matsumoto and T. Uchida, Chem. Lett., 1981, 1673.
12. (c) S. Hashimoto, K. Matsumoto and S. Otani, J. Org. Chem., 1984, 49, 4543.
13. (a) K. Matsumoto, Angew. Chem., Int. Ed. Engl., 1981, 20, 770.
14. (b) K. Matsumoto, Angew. Chem., Int. Ed. Engl., 1984, 23, 617.
15. S. Kobayashi, Synlett, 1994, 689.
16. B. S. El'yanov and E. M. Vasylvitskaya, Rev. Phys. Chem. Jpn, 1980, 50, 169.
17. A. Pross and S. S. Shaik, J. Am. Chem. Soc., 1982, 104, 1129.
18. T. Moriyoshi and K. Mikami, Rev. Phys. Chem. Jpn., 1968, 38, 50.
19. To yield measurable reaction rates, temperature (51.0°C) and base concentration were increased.
20. For a more detailed comment on energy versus volume considerations see: W. J. le Noble and H. Kelm, Angew. Chem., Int. Ed. Engl., 1980, 19, 841.
21. The earliness versus lateness of the transition state has been discussed theoretically: S. Hoz, Acc. Chem. Res., 1993, 26, 69.
22. G. Jenner and R. Ben Salem, Rev. High Press. Sci. Technol., 1998, 7, 1265.
23. G. Jenner, New J. Chem., 1995, 19, 173.
24. The lanthanide catalyst would act like transition metal complexes, which were also found to catalyze Michael reactions: K. Watanabe, K. Miyazu and K. Irie, Bull. Chem. Soc. Jpn., 1982, 55, 3212.
25. H. Kotsuki and K. Arimura, Tetrahedron Lett., 1997, 38, 7583.
26. Jenner, in Organic High Pressure Chemistry, ed. W. J. le Noble, Elsevier, Amsterdam, 1988, p. 143.
27. S. Babb, Rev. Mod. Phys., 1963, 35, 400.
28. T. Urbanski, Synthesis, 1974, 613.
29. N. E. Agafonov, I. P. Sedishev, A. V. Dudin, A. A. Kutin, G. A. Stashina and V. M. Zhulin, Izv. Akad. Nauk SSR, Ser. Khim., 1991, 426.
30. D. Simoni, F. P. Invidiata, S. Manfredini, R. Ferroni, I. Lampronti, M. Roberti and G. P. Pollini, Tetrahedron Lett., 1997, 38, 2749.