The first, general, highly efficient method for preparing tetrasubstituted epoxides using HOF·CH3CN

European Journal of Organic Chemistry

Volumn , Issue 10, 2003, Pages 1915-1917

  Rozen, Shlomo ^a   Golan, Elizabeth ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Epoxidations; Fluorine; HOF CH3CN; Olefins; Synthetic methods

Indexed keywords

1,2 EPOXYCYCLOHEXANE 1,2 DICARBOXYLATE; 2 EPOXY 3 ETHYL 2 METHYL 4 OXOCYCLOHEXANE 1 CARBOXYLATE; 2,3 DIMETHYL 2,3 EPOXYMALEATE; 2,3 EPOXY 2,3,4,5 TETRAMETHYLCYCLOPENTANONE; 9 HYDROXY 10 ACETAMIDODECALIN; 9,10 EPOXYDECALIN; ACETONITRILE; ALKENE DERIVATIVE; EPOXIDE; FLUORINE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; EPOXIDATION; OXYGEN TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037573551     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300082     Document Type: Article

References (15)

1. The challenge for developing such a method was presented to one of us (S. R.) by the late Prof. D. H. R. Barton a few days before his death.
2. 3CN can be found in: S. Dayan, Y. Bareket, S. Rozen, Tetrahedron 1999, 55, 3657-3664.
3. S. Rozen, Acc. Chem. Res. 1996, 29, 243-248.
4. S. Rozen, Y. Bareket, M. Kol, Tetrahedron 1993, 49, 8169-8178. Baeyer's mechanism was presented in: A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625, and then was disqualified in: W. E. von Doering, E. Dorfman, J. Am. Chem. Soc. 1953, 75, 5595.)
5. S. Rozen, Y. Bareket, M. Kol, Tetrahedron 1993, 49, 8169-8178. Baeyer's mechanism was presented in: A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625, and then was disqualified in: W. E. von Doering, E. Dorfman, J. Am. Chem. Soc. 1953, 75, 5595.)
6. S. Rozen, Y. Bareket, M. Kol, Tetrahedron 1993, 49, 8169-8178. Baeyer's mechanism was presented in: A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625, and then was disqualified in: W. E. von Doering, E. Dorfman, J. Am. Chem. Soc. 1953, 75, 5595.)
7. S. Rozen, S. Dayan, Angew. Chem. Int. Ed. 1999, 38, 3471-3473.
8. G. Rio, B. Muller, F. Lareze, C. R. Acad. Sci. Paris, Ser. C 1969, 268, 1157-1159.
9. W. Adam, L. Hadjiarapoglou, A. Smerz, Chem. Ber. 1991, 124, 227-232.
10. R. M. Moriarty, S. C. Gupta, H. Hu, D. R. Berenschot, K. B. White, J. Am. Chem. Soc. 1981, 103, 686-688.
11. This epoxide has been prepared by treating 20 with DMDO for 24 h: S. E. Denmark, D. C. Forbes, D. S. Hays, J. S. DePue, R. G. Wilde, J. Org. Chem. 1995, 60, 1391-1407.
12. R. D. Chambers, A. M. Kenwright, M. Parsons, G. Sandford, J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1 2002, 2190-2197.
13. [11a] S. Dagan, A. Amirav, J. Am. Soc. Mass. Spectrom. 1995, 6, 120-131.
14. A. Amirav, A. Gordin, N. Tzanani, Rapid Commun. Mass Spectrom. 2001, 15, 811-820.
15. S. Dayan, M. Kol, S. Rozen, Synthesis 1999, 1427-1430.