An easy way for constructing hard-to-make epoxides employing HOF·CH3CN

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3397-3399

  Golan, Elizabeth ^a   Hagooly, Aviv ^a   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Epoxides; F2; HOF CH3CN

Indexed keywords

ALKENE DERIVATIVE; EPOXIDE;

ARTICLE; CHEMICAL REACTION; EPOXIDATION; OXYGEN TRANSPORT;

EID: 1842687917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.030     Document Type: Article

References (22)

1. Prakash G.K.S., Etzkorn M. Angew. Chem., Int. Ed. 43:2004;26-28.
2. 3CN can be found in: Dayan S., Bareket Y., Rozen S. Tetrahedron. 55:1999;3657-3664.
3. Rozen S., Carmeli M. J. Am. Chem. Soc. 125:2003;8118-8119.
4. Dayan S., Kol M., Rozen S. Synthesis. 1999;1427-1430.
5. Rozen S., Dayan S. Angew. Chem., Int. Ed. 38:1999;3471-3473.
6. Dayan S., Ben-David I., Rozen S. J. Org. Chem. 65:2000;8816-8818.
7. Rozen S., Kol M. J. Org. Chem. 55:1990;5155-5159.
8. Rozen S., Bareket Y., Dayan S. Tetrahedron Lett. 37:1996;531-534.
9. Rozen S., Bareket Y., Blum J. Tetrahedron Lett. 38:1997;2333-2334.
10. Rozen S., Golan E. Eur. J. Org. Chem. 2003;1915-1917.
11. Rozen S. Acc. Chem. Res. 29:1996;243-248.
12. Ruecker C., Seppelt W., Fritz H., Prinzbach H. Chem. Ber. 117:1984;1801-1833.
13. 2 in inert gases are commercially available, simplifying the process. If elementary precautions are taken, work with fluorine is relatively simple and we have had no bad experiences working with it.
14. 3 solution on a FTIR spectrophotometer. The spectral properties of all known products are in excellent agreement with their structures, and are consistent with those described in the literature.
15. Murray R.W., Singh M., Rath N.P. Tetrahedron. 55:1999;4539-4558.
16. Alder K., Flock F.H., Beumling H. Chem. Ber. 93:1960;1896-1899.
17. Basselier J.J., Le Roux J.P. Bull. Soc. Chim. Fr. 12:1971;4448-4454.
18. 9: C, 53.93; H, 5.66. Found: C, 54.29; H, 5.61.
19. 4.monohydrate: C, 41.10; H, 4.14. Found: C, 40.57; H, 4.19.
20. Rozen S., Bareket Y. Chem. Commun. 1996;627-628.
21. Moriarty R.M., Prakash O., Musallam H.A. J. Heterocycl. Chem. 22:1985;583-584.
22. 3: C, 69.46; H, 5.30. Found: C, 69.57; H, 5.40.