Highly efficient epoxidation of electron-deficient olefins with tetrabutylammonium peroxydisulfate

Tetrahedron

Volumn 63, Issue 24, 2007, Pages 5184-5188

  Yang, Seung Gak ^a   Hwang, Je Pil ^a   Park, Min Young ^a   Lee, Kieseung ^b   Kim, Yong Hae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Woosuk University   (South Korea)

Author keywords

Electron deficient olefins; Epoxidation; Hydrogen peroxide; Tetrabutylammonium peroxydisulfate

Indexed keywords

2,3 EPOXY 1,3 DIPHENYLPROPANONE; 2,3 EPOXY 2,3 DIHYDRO 1,4 NAPHTHOQUINONE; 2,3 EPOXY 3 PHENYLPROPANAL; 2,3 EPOXY 3,7 DIMETHYL 6 OCTENAL; 2,3 EPOXY 5 ISOPROPENYL 2 METHYLCYCLOHEXANONE; 2,3 EPOXYCYCLOHEXANONE; 2,3 EPOXYCYCLOPENTONE; 3,4 EPOXY 4 PHENYL 2 BUTANONE; 3,4 EPOXY 6 PHENYL 2 HEXANONE; ACETONITRILE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; CINNAMALDEHYDE; HYDROGEN PEROXIDE; METHANOL; SODIUM HYDROXIDE; SULFATE; TETRABUTYLAMMONIUM PEROXYDISULFATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; EPOXIDATION; PRIORITY JOURNAL;

EID: 34247871204     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.167     Document Type: Article

References (27)

1. Jacobsen E.N. Acc. Chem. Res. 33 (2000) 421-431
2. Porter M.J., and Skidmore J. Chem. Commun. (2000) 1215-1225
3. Yadav V.K., and Kapoor K.K. Tetrahedron 51 (1995) 8573-8584
4. Smith M.B., and March J. March's Advanced Organic Chemistry. 5th ed. (2001), John Wiley, New York, NY pp 1051-1054
5. Miyashita M., Suzuki T., and Yoshikoshi A. Chem. Lett. (1987) 285-288
6. Garcia R.J.L., Fajardo C., Fraile A., and Martin M.R. J. Org. Chem. 70 (2005) 4300-4306
7. Lygo B., and Wainwright P.G. Tetrahedron Lett. 39 (1998) 1599-1602
8. Straub T.S. Tetrahedron Lett. 36 (1995) 663-664
9. McQuaid K.M., and Pettus T.R.R. Synlett (2004) 2403-2405
10. Yang D., Wong M.-K., and Yip Y.-C. J. Org. Chem. 60 (1995) 3887-3889
11. Kim Y.H., and Chung B.C. J. Org. Chem. 48 (1983) 1564-1565
12. Jung J.C., Choi H.C., and Kim Y.H. Tetrahedron Lett. 34 (1993) 3581-3584
13. Choi H.C., and Kim Y.H. Synth. Commun. 24 (1994) 2307-2311
14. Choi H.C., Jung J.C., Cho K.I., and Kim Y.H. Heteroat. Chem. 6 (1995) 333-338
15. Choi H.C., Cho K.I., and Kim Y.H. Synlett (1995) 207-208
16. Hwang J.P., Yang S.G., and Kim Y.H. Chem. Commun. (1997) 1355-1356
17. Kim Y.H., Hwang J.P., and Yang S.G. Tetrahedron Lett. 38 (1997) 3009-3012
18. Starting material was recovered quantitatively.
19. Payne G.B. J. Am. Chem. Soc. 81 (1959) 4901-4904
20. Payne G.B. J. Org. Chem. 25 (1960) 275-276
21. Payne G.B. J. Org. Chem. 26 (1961) 250-252
22. Kim, Y. H.; Yang, S. G., unpublished results.
23. Reed K.L., Gupton J.T., and Solarz T.L. Synth. Commun. 19 (1989) 3579-3587
24. Lakouraj M.M., Movassagh B., and Bahrami K. Synth. Commun. 31 (2001) 1237-1242
25. Cella J.A., McGrath J.P., Kelley J.A., El Soukkary O., and Hilpert L. J. Org. Chem. 42 (1977) 2077-2080
26. Marmor S. J. Org. Chem. 28 (1963) 250-251
27. Aldrich Catalogue Hand Book of Fine Chemicals (1996-1997) p 1372