[2 + 2] Photocycloadditions and photorearrangements of 2- alkenylcarboxamido-2-cycloalken-1-ones

Tetrahedron

Volumn 56, Issue 26, 2000, Pages 4479-4489

  Meyer, Catherine ^a   Piva, Olivier ^a,b   Pete, Jean Pierre ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Amides; Cyclohexenones; Cyclopentenones; Lactams; Photocycloaddition

Indexed keywords

CYCLOALKENE;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0034705386     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00366-5     Document Type: Article

References (39)

1. (a) Cossy, J.; Carrupt, P. A.; Vogel, P. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed. Wiley: New York, NY, USA, 1989; pp 1369-1565.
2. (b) Becker, D.; Haddad, N. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, NY, USA, 1989; Vol. 10; pp 1-162.
3. (c). De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359.
4. Schuster D., Lem G., Kaprinidis N.A. Chem. Rev. 93:1993;3.
5. Crimmins M.T. Chem. Rev. 88:1988;1453.
6. (a) Le Blanc, S.; Pete, J. P.; Piva, O. Tetrahedron Lett. 1993, 34, 635.
7. (b) Piva-Le Blanc, S.; Pete, J.-P.; Piva, O. Chem. Commun. 1998, 235.
8. Faure S., Piva-Le Blanc S., Piva O., Pete J.P. Tetrahedron Lett. 38:1997;1045.
9. (a) Becker, D.; Haddad, N. Tetrahedron 1993, 49, 947.
10. (b) Matlin, A. R.; Georges, C. F.; Agosta, W. C. J. Am. Chem. Soc. 1986, 108, 3385.
11. (c) Wolff, S.; Agosta, W.C. J. Am. Chem. Soc. 1983, 105, 1299.
12. Takahashi M., Uchino T., Ohno K., Tamura Y., Ikeda M. J. Org. Chem. 48:1983;4241.
13. Ikeda M., Uchino T., Takahashi M., Ishibashi H., Tamura Y., Kido M. Chem. Pharm. Bull. 33:1985;3279.
14. Arnould J.C., Cossy J., Pete J.P. Tetrahedron. 36:1980;1585.
15. Part of this work was published in a preliminary communication. Meyer, C.; Piva, O.; Pete, J.P. Tetrahedron Lett. 1996, 37, 5885.
16. Schultz A.G., Holobosky M.A. Tetrahedron Lett. 34:1993;3021.
17. (a) Cossy, J.; Thellend, A. Synthesis 1989, 753.
18. (b) Cossy, J.; Bellotti, A.; Bouzide, A.; Thellend, A. Bull. Soc. Chim. Fr. 1994, 131, 723.
19. (a) Reich, H. J.; Wollowitz, S. In Organic Reactions; Paquette, L. A., Ed.; Wiley, NY, New York, USA, 1993; Vol. 44; pp 1-296.
20. (b) Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar III, K. S. J. Org. Chem. 1981, 46, 2920.
21. Wagner P.J., Park B.S. Padwa A., Organic Photochemistry. Vol. 11:1991;309-333 Marcel Dekker, New York, NY, USA.
22. (a) Wagner, P. J.; Meador, M. A.; Park, B. S. J. Am. Chem. Soc. 1990, 112, 5199.
23. (b) Descotes, G. Bull. Soc. Chim. Belges 1982, 91, 973.
24. (c) Descotes, G. Topics Curr. Chem. 1990, 154, 41.
25. Wyss C., Batra R., Lehmann C., Sauer S., Giese B. Angew. Chem. Int. Ed. Engl. 35:1996;2529.
26. Xu W., Mariano P.S. J. Am. Chem. Soc. 113:1991;1431. (and references therein).
27. Ab initio calculations were performed using B3LYP/6-31G//HF/3-21G.
28. (a) Factors favouring hydrogen transfer to the α- or β-carbon atom of enones have already been discussed, see: Byrne, B.; Wilson II, C. A.; Wolff, S.; Agosta, W.C. J. Chem. Soc. Perkin Trans. 1 1978, 1550.
29. (b) Intramolecular electron transfer might explain the observed hydrogen migrations and the labeling experiments. Cf.: (c) Gloor, J.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1971, 54, 1864.
30. (d) Gloor, J.; Schaffner, K. Helv. Chim. Acta 1974, 57, 1815.
31. (e) Gloor, J.; Bernardinelli, G.; Gerdil, R.; Schaffner, K. Helv. Chim. Acta 1973, 56, 2520.
32. (f) Nobs, F., Burger, U., Schaffner, K. Helv. Chim. Acta 1977, 60, 1607.
33. Eilingsfeld H. Chem. Ber. 96:1963;2899.
34. Barton D.H.R., Hansen P.E., Picker K. J. Chem. Soc., Perkin Trans. 1:1977;1723.
35. Rynbrandt R.H., Schmidt F.L. J. Med. Chem. 1971;54.
36. Cordonnier G., Sliwa H. J. Heterocycl. Chem. 24:1987;111.
37. (a) Froborg, J.; Magnusson, G. J. Am. Chem. Soc. 1978, 100, 6728.
38. (b) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 1621.
39. (c) Liu, H. J.; Ulibarri, G.; Browne, E.N.C. Can. J. Chem. 1992, 70, 1545.