Highly effective peroxidic epoxidation of olefins using hexathiocyanatorhenate(IV) as catalyst and bicarbonate as co-catalyst

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 339-341

  Dinda, Subhajit ^a   Roy Chowdhury, Sujoy ^a   Abdul Malik, K M ^b   Bhattacharyya, Ramgopal ^a  

^a JADAVPUR UNIVERSITY   (India)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Catalyst; Co catalyst; Efficient epoxidation; Hexathiocyanatorhenate(IV); Sodium bicarbonate

Indexed keywords

ALKENE DERIVATIVE; BICARBONATE; HYDROGEN PEROXIDE; OXIDIZING AGENT; THIOCYANIC ACID DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; EPOXIDATION; OXIDATION KINETICS;

EID: 10044273218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.163     Document Type: Article

References (32)

1. G. Grigoropoulou, J.H. Clark, and J.A. Elings Green Chem. 5 2003 1 7
2. S.L.H. Rebelo, M.M.Q. Simões, M.G.P.M.S. Neves, A.M.S. Silva, and J.A.S. Cavaleiro Chem. Commun. 2004 608 609
3. W. Adam Peroxide Chemistry-Mechanistic and Preparative Aspects of Oxygen Transfer 2000 Wiley-VCH Weinheim, FRG
4. K. Sato, M. Aoki, and R. Noyori Science 281 1998 1646 1647
5. K.A. Jorgensen Chem. Rev. 89 1989 431 458
6. C.W. Jones Applications of Hydrogen Peroxide and Derivatives 1999 MPG Books Ltd Cornwall, UK
7. 2 see: methyltrioxorhenium: J. Rudolph, K.L. Reddy, J.P. Chiang, and K.B. Sharpless J. Am. Chem. Soc. 119 1997 6189 6190
8. W.A. Hermann, R.W. Fischer, and D.W. Marz Angew. Chem., Int. Ed. Engl. 30 1991 1638 1641
9. Tungsten complexes including heteropolyoxo tungstates: X. Zuwei, Z. Ning, S. Yu, and L. Kunlan Science 292 2001 1139 1141
10. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, and R. Noyori J. Org. Chem. 61 1996 8310 8311
11. C. Venturello, E. Alneri, and M. Ricci J. Org. Chem. 68 1983 3831 3833
12. C. Venturello, R.D. Aloiso, J.C. Bart, and M. Ricci J. Mol. Catal. 32 1985 107 110
13. Mn-complexes: A. Berkessel, and C.A. Sklorz Tetrahedron Lett. 40 1999 7965 7968
14. D. de Vos, and T. Bein Chem. Commun. 1996 917 918
15. B.S. Lane, and K. Burgess Chem. Rev. 103 2003 2457 2473 and references cited therein
16. J. Brinksma, L. Schmeider, G. van Vliet, R. Boaron, R. Hage, D.E. de Vos, P.L. Alsters, and B.L. Feringa Tetrahedron Lett. 43 2002 2619 2622
17. Fe-complexes: M.C. White, A.G. Doyle, and E.N. Jacobsen J. Am. Chem. Soc. 123 2001 7194 7195
18. Mo-complex: (l) see p 354 of Ref. 3
19. H. Mimoun, I. Seree de Roch, and L. Sajus Tetrahedron 26 1970 37 50
20. Ru-complexes: A.S. Goldstein, R.H. Beer, and R.S. Drago J. Am. Chem. Soc. 116 1994 2424 2429
21. (a) See Ref. 6b
22. W.A. Hermann, and F.E. Kühn Acc. Chem. Res. 30 1997 169 180
23. H. Adolfson, A. Converso, and K.B. Sharpless Tetrahedron Lett. 40 1999 3991 3994
24. + cations, the anion (the catalyst precursor) having an octahedral geometry
25. S. Banfi, F. Legramandi, P. Montanari, G. Possi, and S. Quici Chem. Commun. 1991 1285 1287
26. -1) for the epoxidation of 1-phenyl cyclohexene
27. D.E. Richardson, H. Yao, K.M. Frank, and D.A. Bannett J. Am. Chem. Soc. 122 2000 1729 1739
28. B.S. Lane, M. Vogt, V.J. de Rose, and K. Burgess J. Am.Chem. Soc. 124 2002 11946 11954
29. 4 (A.I. Vogel A Textbook of Quantitative Inorganic Analysis 3rd ed. 1964 ELBS and Longmans, Green and Co. London) and the latter as Nitron perrhenate (
30. -(pπ*)→Re(5dπ) LMCT transition
31. W.A. Hermann, R.W. Fischer, W. Scherer, and M.U. Rauch Angew. Chem., Int. Ed. Engl. 32 1993 1157 1160
32. R. Bandyopadhyay, S. Biswas, S. Guha, A.K. Mukherjee, and R. Bhattacharyya Chem. Commun. 1999 1627 1628