Ring-opening fluorination of epoxides using hydrofluoric acid and additives

Journal of Fluorine Chemistry

Volumn 99, Issue 2, 1999, Pages 95-97

  Shimizu, Makoto ^a   Nakahara, Yuko ^b  

^a MIE UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Epoxide; Fluorohydrin; Hydrofluoric acid; Silicon tetrafluoride

Indexed keywords

EID: 0042943522     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(99)00180-3     Document Type: Article

References (24)

1. Yoneda N. Tetreahedron. 47:1991;5329.
2. M. Kuroboshi, T. Hiyama, Synlett (1991) 185.
3. Sharts C.M., Sheppard W.A. Org. Reactions. 21:1974;125.
4. G.A. Olah, X.-Y. Li, Synlett (1990) 267.
5. Olah G.A., Welch J.T., Vankar Y.D., Nojima M., Kerekes I., Olah J.A. J. Org. Chem. 44:1979;3872.
6. G. Aranda, J. Jullien, J.A. Martin, Bull. Soc. Chim. France (1965) 1890.
7. Kanemoto S., Shimizu M., Yoshioka H. Bull. Chem. Soc. Jpn. 62:1989;2024.
8. S. Kanemoto, M. Shimizu, H. Yoshioka, J. Chem. Soc., Chem. Commun. (1989) 690.
9. Shimizu M., Chang G., Yoshioka H. J. Fluorine Chem. 41:1988;245.
10. Kanemoto S., Shimizu M., Yoshioka H. Tetrahedron Lett. 28:1987;663.
11. Shimizu M., Yoshioka H. Tetrahedron Lett. 28:1987;3119.
12. Kanemoto S., Shimizu M., Yoshioka H. Tetrahedron Lett. 28:1987;6313.
13. Shimizu M., Nakahara Y., Yoshioka H. J. Fluorine Chem. 97:1999;57.
14. Shimizu M. Encyclopedia of Reagents for Organic Synthesis. 6:1995;4442-4444.
15. M. Shimizu, Y. Nakahara, H. Yoshioka, J. Chem. Soc., Chem. Commun. (1989) 1881.
16. Shimizu M., Yoshioka H. Tetrahedron Lett. 30:1989;967.
17. Shimizu M., Yoshioka H. Heterocycles. 27:1988;2527.
18. Shimizu M., Yoshioka H. Tetrahedron Lett. 29:1988;4101.
19. A.I. Ayi, R. Guegj, J. Chem. Soc. Perkin I (1983) 2045.
20. Alvernhe G.M., Ennakoua C.M., Lacombe S.M., Laurent A.J. J. Org. Chem. 46:1981;4938.
21. Alvenhe G., Kozolowska-Gramsz E., Lacombe-Bar S., Laurent A.J. Tetrahedron Lett. 19:1978;5203.
22. Richborn B., Gerkin R. J. Am. Chem. Soc. 93:1971;1963.
23. Coxon J.N., Harshorn M.P., Rae W.J. Tetrahedron. 26:1970;1091.
24. Hart H., Lerner L.R. J. Org. Chem. 72:1967;2669.