Ring opening of tetrahydrofurans with Phenyl trimethylsilyl selenide catalyzed by moist zinc iodide

Synthesis (Germany)

Volumn 1988, Issue 3, 1988, Pages 175-178

  Miyoshi, Noritaka ^a   Hatayama, Yoshio ^a   Ryu, Ilhyong ^a   Kambe, Nobuaki ^a   Murai, Toshiaki ^a   Murai, Shinji ^a   Sonoda, Noboru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 12644289711     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1988-27505     Document Type: Article

References (23)

1. Miyoshi, N., Ishii, H., Kondo, K., Murai. S., Sonoda, N. Synthesis 1979, 300.
2. Detty, M. R., Seidler, M. D. J. Org. Chem. 1981, 46, 1283.
3. Detty, M. R. Tetrahedron Lett. 1978, 5087.
4. Detty, M. R. J. Org. Chem. 1980, 45, 80.
5. Drake, J. E., Hemmings, R. T. J. Chem. Soc. Dalton Trans. 1976, 1730.
6. Liotta, D., Paty, P. B., Johnston, J., Zima, G. Tetrahedron Lett. 1978, 5091.
7. Derkach, N. Y., Pasmurtseva, N. A., Lercbenko, E. S. Zh. Org. Khim. 1971, 7, 1543;
8. C. A. 1971, 75, 263.
9. Miyoshi, N., Ishii, H., Murai, S., Sonoda, N. Chem. Lett. 1979, 873.
10. Kuwajima, I., Hoshino, S., Tanaka, T., Shimizu, M. Tetrahedron Lett. 1980, 3209.
11. Dumont, W., Krief, A. Angew. Chem. 1976, 88, 184;
12. Angew. Chem. Int. Ed. Engl. 1976, 15, 161.
13. Dumont, W., Krief, A. Angew. Chem. 1977, 89, 559;
14. Angew. Chem. Int. Ed. Engl. 1977, 16, 540.
15. Suzuki, M., Kawagishi, T., Noyori, R. Tetrahedron Lett. 1981, 22, 1809.
16. Miyoshi, N., Kondo, K., Murai, S., Sonoda, N. Chem. Lett. 1979, 909.
17. Detty, M. R. Tetrahedron Lett. 1979, 4189.
18. For a recent review, see: Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis, Pergaraon Press, Oxford, 1986.
19. Liotta, D. (ed.) Organoselenium Chemistry, John Wiley & Sons, New York, 1987.
20. The precise role of the added water is not clear, but we believe that the coordination of water to the zinc atom possibly increases the activity of the catalyst.
21. The reaction fo 2, 4-dimethyltetrahydrofuran with silyl selenide was much slower and required 50 h at 40 C for 80% conversion.
22. Eliel, E. L., Pillar, C. J. Am. Chem. Soc. 1955, 77, 3600.
23. Colonge, J., Marey, R. Org. Synth. Coll. Vol. IV 1963, 350, 601.