Rapid and highly selective epoxidation of alkenes by tetrabutylammonium monopersulfate in the presence of manganese meso-tetrakis(pentafluorophenyl)porphyrin and tetrabutylammonium salts or imidazole co-catalysts

Tetrahedron Letters

Volumn 47, Issue 39, 2006, Pages 7007-7010

  Mohajer, Daryoush ^a   Solati, Zahra ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Co catalyst; Epoxidation; Manganese porphyrin; Tetrabutylammonium monopersulfate; Tetrabutylammonium salt

Indexed keywords

ALKENE DERIVATIVE; IMIDAZOLE DERIVATIVE; PORPHYRIN DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 33747794090     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.119     Document Type: Article

References (33)

1. Groves J.T., Nemo T.E., and Myers R.S. J. Am. Chem. Soc. 101 (1979) 1032-1033
2. Gross Z., and Mahammed A. J. Mol. Catal. A: Chem. 142 (1999) 367-372
3. Tabushi I., and Korga N. Tetrahedron Lett. 20 (1979) 3681-3684
4. Meunier B., Guilmet E., De Carvalho M.-E., and Poilblanc R. J. Am. Chem. Soc. 106 (1984) 6668-6676
5. Renaud J.P., Battioni P., Bartoli J.F., and Mansuy D. J. Chem. Soc., Chem. Commun. (1985) 888-889
6. Battioni P., Renaud J.P., Bartoli J.F., and Mansuy D. J. Chem. Soc., Chem. Commun. (1986) 341-343
7. Mohajer D., and Hosseini Monfared H. J. Chem. Res. (S) (1998) 772-773
8. Mohajer D., Karimipor G., and Bagherzadeh M. New J. Chem. 23 (2004) 740-747
9. Takata T., and Ando W. Tetrahedron Lett. 24 (1983) 3631-3634
10. Suslick K.S., Acholla F.V., and Cook B.R. J. Am. Chem. Soc. 109 (1987) 2818-2819
11. Mohajer D., and Bagherzadeh M. J. Chem. Res. (S) (1998) 556-557
12. Mohajer D., Tayebi R., and Goudarziafshar H. J. Chem. Res. (S) (1999) 168-169
13. Mohajer D., and Tangestaninejad S. J. Chem. Soc., Chem. Commun. (1993) 240-241
14. Robert A., and Meunier B. New J. Chem. 12 (1988) 885-895
15. De Porter B., and Meunier B. J. Chem. Soc., Perkin Trans. 2 (1985) 1735-1740
16. Commarota L., Campestrini S., Carrier M., Di Furia F., and Ghiotti P. J. Mol. Catal. A: Chem. 137 (1999) 155-160
17. Mohajer D., and Rezaeifard A. Tetrahedron Lett. 43 (2002) 1881-1884
18. Meunier B. Inorg. Chem. 27 (1988) 161-164
19. Mohajer D., and Tangestaninejad S. Tetrahedron Lett. 35 (1994) 945-948
20. Baciocchi E., Boschi T., Galli C., Lapi A., and Tagliatesta P. Tetrahedron 53 (1997) 4497-4502
21. Konishi K., Oda K., Nishida K., Aida T., and Inoue S. J. Am. Chem. Soc. 114 (1992) 1313-1318
22. Guilment E., and Meunier B. Tetrahedron Lett. 23 (1982) 2449-2452
23. Mansuy D., Battioni P., and Renaud J.P. J. Chem. Soc., Chem. Commun. (1985) 155-157
24. Thellend A., Battioni P., and Mansuy D. J. Chem. Soc., Chem. Commun. (1994) 1035-1036
25. Rebelo S.L.H., Simões M.M.Q., Neves M.G.M.S., and Cavaleiro J.A.S. J. Mol. Catal. A: Chem. 201 (2003) 9-22
26. Ellis Jr. P.E., and Lyons J.E. J. Chem. Soc., Chem. Commun. (1989) 1315-1316
27. Collman J.P., Chein A.S., Eberspacher T.A., Zhong M., and Brauman J.I. Inorg. Chem. 39 (2000) 4625-4629
28. Rocha Gansalves A.-M.dA., Johnstone R.-A.W., Pereira M.-M., and Shaw J. J. Chem. Soc., Perkin Trans. 1 (1991) 645-649
29. 5 should be considered as a potential explosive
30. 2 = meso-tetrakis(2,6-dichlorophenyl)porphyrin (Hoffman, P.; Robert, A.; Meunier, B. Bull. Soc. Chim. Fr. 1992, 129, 85-97); MnTPFPP(OAc) (Kadish, K. M.; Araullo-McAdams, C.; Han, B. C.; Franzen, M. M. J. Am. Chem. Soc. 1990, 112, 8364-8368); MnTPP(OAc), MnTMP(OAc), and MnTDCPP(OAc) (Adler, A. D.; Longo, F. R.; Kampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443-2445).
31. 4NBr were purchased from Fluka.
32. 254, Merck, on a 20 cm × 20 cm plate) using n-hexane-ethyl acetate (7:1, v:v) as the mobile phase. For the separation of the cyclohexene oxide a silica gel column (silica gel 40, mesh 70-230, Fluka, in n-hexane), and n-hexane-ethyl acetate (7:1, v:v) eluent was used.
33. Rebelo S.H., Pereira M.M., Simões M.M.Q., Neves M.G.M.S., and Cavaleiro J.A.S. J. Catal. 234 (2005) 76-87