Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant

Journal of Molecular Catalysis A: Chemical

Volumn 277, Issue 1-2, 2007, Pages 53-60

  Baxová, Lenka ^a   Cibulka, Radek ^a   Hampl, František ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Flavinium salts; Green chemistry; Micelles; Organocatalysis; Sulfoxidation

Indexed keywords

CATALYSIS; MICELLES; PH EFFECTS; REACTION RATES; SALTS;

FLAVINIUM SALTS; GREEN CHEMISTRY; HEXADECYLTRIMETHYLAMMONIUM NITRATE; ORGANOCATALYSIS;

SULFONATION;

EID: 35348824234     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2007.07.027     Document Type: Article

References (51)

1. Hudlický M. Oxidation in Organic Chemistry (1990), ACS, Washington DC pp. 252-259
2. Carreño M.C. Chem. Rev. 95 (1995) 1717-1760
3. Fernández I., and Khiar N. Chem. Rev. 103 (2003) 3651-3705
4. Rouhi A.M. Chem. Eng. News 81 19 (2003) 56-61
5. Caron S., Dugger R.W., Ruggeri S.G., Ragan J.A., and Ripin D.H.B. Chem. Rev. 106 (2006) 2943-2989
6. Bäckvall J.-E. In: Bäckvall J.-E. (Ed). Modern Oxidation Methods (2004), Wiley-VCH Verlag, Weinheim 193-222
7. Hill C.L. Angew. Chem. Int. Ed. 43 (2004) 402-404
8. Gelalcha F.G. Chem. Rev. 107 (2007) 3338-3361
9. Palfey B., and Massey V. In: Sinnott M. (Ed). Comprehensive Biological Catalysis vol. 3 (1998), Academic Press, London 83-154
10. In: Müller F. (Ed). Chemistry and Biochemistry of Flavoenzymes (1991), CRC, Boca Raton, FL
11. Moonen M.J.H., Fraaije M.W., Rietjens I.M.C.M., Laane C., and van Berkel W.J.H. Adv. Synth. Catal. 10 (2002) 1023-1035
12. Bruice T.C. Acc. Chem. Res. 13 (1980) 256-262
13. Ball S., and Bruice T.C. J. Am. Chem. Soc. 101 (1979) 4017-4019
14. Ball S., and Bruice T.C. J. Am. Chem. Soc. 102 (1980) 6498-6503
15. Bergstat K., and Bäckvall J.-E. J. Org. Chem. 63 (1998) 6650-6655
16. Minidis A.B.E., and Bäckvall J.-E. Chem. Eur. J. 7 (2001) 297-302
17. Lindén A.A., Krüger L., and Bäckvall J.-E. J. Org. Chem. 68 (2003) 5890-5896
18. Lindén A.A., Hermanns N., Ott S., Krüger L., and Bäckvall J.-E. Chem. Eur. J. 11 (2005) 112-119
19. Imada Y., Iida H., Ono S., and Murahashi S.-I. J. Am. Chem. Soc. 125 (2003) 2868-2869
20. Mazzini C., Lebreton J., and Furstoss R. J. Org. Chem. 61 (1996) 8-9
21. Imada Y., Iida H., Murahashi S.-I., and Naota T. Angew. Chem. Int. Ed. 44 (2005) 1704-1706
22. Shinkai S., Yamaguchi T., Manabe O., and Toda F. Chem. Commun. (1988) 1399-1401
23. Murahashi S.-I. Angew. Chem. Int. Ed. 34 (1995) 2443-2465
24. Murahashi S.-I., Ono S., and Imada Y. Angew. Chem. Int. Ed. 41 (2002) 2366-2368
25. Lindén A.A., Johansson M., Hermanns N., and Bäckvall J.-E. J. Org. Chem. 71 (2006) 3849-3853
26. Fendler J.H., and Fendler E.J. Catalysis in Micellar and Macromolecular Systems (1975), Academic Press, New York
27. Vriezema D.M., Aragonès M.C., Elemans J.A.A.W., Cornelissen J.J.L.M., Rowan A.E., and Nolte R.J.M. Chem. Rev. 105 (2005) 1445-1489
28. Hill C.L. Nature 401 (1999) 436-437
29. Anastas P.T., and Warner J.C. Green Chemistry: Theory and Practice (1998), Oxford University Press, Oxford
30. The equilibrium between salt 1 and 4a-hydroxyflavin (1-OH) is a pH dependent process. The formation of 4a-hydroxyflavin (pseudobase) represents addition of water to salt 1 under simultaneous release of proton.
31. Origin 6.1. OriginLab Corporation, Northampton, 2000.
32. Ghisla S., Hartmann U., Hemmerich P., and Müller F. Liebigs Ann. Chem. (1973) 1388-1415
33. Milyaeva N.M. Zh. Neorg. Khim. 3 (1958) 2011-2015
34. Dawber J.G. J. Chem. Soc. A (1968) 1532-1534
35. Micellar binding of an organic substrate is generally described by a binding constant KS = [Sm]/[Sw][Dn], where [Sm] and [Sw] is the concentration of the substrate in micellar and aqueous phase, respectively, and [Dn] is the concentration of micellized surfactant.
36. Sepulveda L., Lissi E., and Quina F. Adv. Colloid Interf. Sci. 25 (1986) 1-57
37. Blaskó A., Bunton C.A., and Wright S. J. Phys. Chem. 97 (1993) 5435-5442
38. Bosco Bharathy J.R., Ganesan T.K., Rajkumar E., Rajagopal S., Manimaran B., Rajendran T., and Lu K.-L. Tetrahedron 61 (2005) 4679-4687
39. Mager H.I.X., and Tu S.-C. Tetrahedron 50 (1994) 5287-5298
40. Yoneda F., Sakuma Y., Ichiba M., and Shinomura K. J. Am. Chem. Soc. 98 (1976) 830-835
41. Hemmerich P., Prijs B., and Erlenmeyer H. Helv. Chim. Acta 48 (1960) 372-394
42. Cibulka R., Vasold R., and König B. Chem. Eur. J. 10 (2004) 6223-6231
43. Scrimin P., Tecilla P., Tonellato U., and Bunton C.A. Colloids Surf. A 144 (1998) 71-79
44. Bunton C., Nome F., Quina F.H., and Romsted L.S. Acc. Chem. Res. 24 (1991) 357-364
45. Bhattacharya S., Snehalatha K., and George S.K. J. Org. Chem. 63 (1998) 27-35
46. Mancin F., Tecilla P., and Tonellato U. Langmuir 16 (2000) 227-233
47. Grassert I., Kovács J., Fuhrmann H., and Oehme G. Adv. Synth. Catal. 344 (2002) 312-318
48. Amels P., Elias H., and Wannowius K.-J. J. Chem. Soc. Faraday Trans. 93 (1997) 2537-2544
49. Bach R.D., Su M.-D., and Schlegel H.B. J. Am. Chem. Soc. 116 (1994) 5379-5391
50. Bunton C.A., Nome F.A., Quina F.H., and Romsted L.S. Acc. Chem. Res. 24 (1991) 357-364
51. Merényi G., and Lind J. J. Am. Chem. Soc. 113 (1991) 3146-3153