A mechanistic study of the epoxidation of cinnamic acid by hydrogen peroxide catalysed by manganese l,4,7-trimethyl-l,4,7-triazacyclononane complexes

Journal of Molecular Catalysis A: Chemical

Volumn 219, Issue 2, 2004, Pages 265-272

  Gilbert, Bruce C ^a   Lindsay Smith, John R ^a   Mairata I Payeras, Antoni ^a   Oakes, John ^b   Pons I Prats, Roger ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

1,4,7 Trimethyl 1,4,7 triazacyclononane; Catalysis; Epoxidation; Hydrogen peroxide; Manganese

Indexed keywords

ADDITIVES; DERIVATIVES; ORGANIC ACIDS; ORGANOMETALLICS; OXIDATION; ULTRAVIOLET SPECTROSCOPY;

EPOXIDATION; LIGANDS;

CATALYSIS;

ACETONITRILE; CINNAMIC ACID; HYDROGEN PEROXIDE; LIGAND; MANGANESE; MANGANESE SULFATE; OXALIC ACID; OXIDIZING AGENT; OXYGEN; TRIAZINE DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL LABELING; CHEMICAL REACTION; CORRELATION ANALYSIS; ELECTROSPRAY MASS SPECTROMETRY; EPOXIDATION; SPECIES; ULTRAVIOLET SPECTROSCOPY;

EID: 3242702573     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.05.012     Document Type: Article

References (35)

1. Hage R., Iburg J.E., Kerschner J., Koek J.H., Lempers E.L.M., Martens R.J., Racherla U.S., Russell S.W., Swarthoff T., van Vliet M.R.P., Warnaar J.B., van der Wolf L., Krijnen B. Nature. 369:1994;637
2. De Vos D.E., Bein T. J. Organomet. Chem. 520:1996;195
3. D. De Vos, T. Bein, Chem. Commun. (1996) 917.
4. Quee-Smith V.C., DelPizzo L., Jureller S.H., Kerschner J.L., Hage R. Inorg. Chem. 35:1996;6461
5. De Vos D.E., Sels B.F., Reynaers M., Rao Y.V.S., Jacobs P.A. Tetrahedron Lett. 39:1998;3221
6. De Vos D.E., de Wildeman S., Sels B.F., Grobet P.J., Jacobs P.A. Angew. Chem. Int. Ed. 38:1999;980
7. Berkessel A., Sklorz C. Tetrahedron Lett. 40:1999;7965
8. Brinsksma J., Schmieder L., van Vliet G., Boaron R., Hage R., De Vos D.E., Alsters P.L., Feringa B.L. Tetrahedron Lett. 43:2002;2619
9. C. Zondervan, R. Hage, B.L. Feringa, Chem. Commun. (1997) 419.
10. Gilbert B.C., Kamp N.W.J., Lindsay Smith J.R., Oakes J. J. Chem. Soc. Perkin Trans. 2:1997;2161
11. Gilbert B.C., Kamp N.W.J., Lindsay Smith J.R., Oakes J. J. Chem. Soc. Perkin Trans. 2:1998;1841
12. Barton D.H.R., Choi S.-Y., Hu B., Smith J.A. Tetrahedron. 54:1998;3367
13. Barton D.H.R., Li W., Smith J.A. Tetrahedron Lett. 39:1998;7055
14. Brinksma J., La Crois R., Feringa B.L., Donnoli M.I., Rosini C. Tetrahedron Lett. 42:2001;4049
15. Lindsay Smith J.R., Shul'pin G.B. Tetrahedron Lett. 39:1998;4909
16. Shul'pin G.B., Suss-Fink G., Lindsay Smith J.R. Tetrahedron. 55:1999;5345
17. Shul'pin G.B., Suss-Fink G., Shul'pina L.S. J. Mol. Catal. A Chem. 170:2001;17
18. Bennur T.H., Sabne S., Deshpande S.S., Srinivas D., Sivasanker S. J. Mol. Catal. A Chem. 185:2002;71
19. B.C. Gilbert, J.R. Lindsay Smith, M.S. Newton, J. Oakes, R. Pons i Prats, Org. Biomol. Chem. (2003) 1568.
20. T. Kobayashi, K. Tsuchiya, Y. Nishida, J. Chem. Soc. Dalton Trans. (1996) 2391.
21. Y.V.S. Rao, D.E. De Vos, T. Bein, P.A. Jacobs, Chem. Commun. (1997) 355.
22. De Vos D.E., Meinershagen J.L., Bein T. Angew. Chem. Int. Ed. 35:1996;2211
23. B.C. Gilbert, A. Mairata i Payeras, J.R. Lindsay Smith, J. Oakes, Org. Biomol. Chem. (2004) 1176.
24. Sartori G., Maggi R., Bigi F., Arienti A., Casnati G., Bocelli G., Mori G. Tetrahedron. 48:1992;9483
25. Ritchie C.D., Sager W.F. Prog. Phys. Org. Chem. 2:1964;323
26. J.L. McLain, J. Lee, J.T. Groves, in: B. Meunier (Ed.), Biomimetic Oxidations Catalysed by Transition Metal Complexes, Imperial College Press, London, 2000, Chapter 3, p. 91.
27. B. Meunier (Ed.), Biomimetic Oxidations Catalysed by Transition Metal Complexes, Imperial College Press, London, 2000, Chapter 4, p. 171.
28. Bortolini O., Meunier B. J. Chem. Soc. Perkin Trans. 2:1984;1967
29. Srinivasan K., Michaud P., Kochi J.K. J. Am. Chem. Soc. 108:1986;2309
30. M.S. Newton, D. Phil. thesis, University of York, 1999.
31. Arnoldi C., Citterio A., Minisci F. J. Chem. Soc. Perkin Trans. 2:1983;531
32. Bernadou J., Fabiano A.-S., Robert A., Meunier B. J. Am. Chem. Soc. 116:1994;9375
33. Groves J.T., Lee J., Marla S.S. J. Am. Chem. Soc. 119:1997;6269
34. Groves J.T., Stern M.K. J. Am. Chem. Soc. 110:1988;8628
35. Arasasingham R.D., He G.X., Bruice T.C. J. Am. Chem. Soc. 115:1993;7985