DFT studies on the reaction pathway of the catalytic olefin epoxidation with CpMoCF3 dioxo and oxo-peroxo complexes

Journal of Organometallic Chemistry

Volumn 748, Issue , 2013, Pages 36-45

  Drees, Markus ^a   Hauser, Simone A ^a   Cokoja, Mirza ^a   Kühn, Fritz E ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

DFT; Epoxidation; Mechanism; Metal oxo complex; Molybdenum; TBHP

Indexed keywords

CATALYTIC EPOXIDATION; DFT; METAL-OXO COMPLEX; OLEFIN EPOXIDATION; REACTION PATHWAYS; TBHP; TERT-BUTYLHYDROPEROXIDE; TRANSITION STATE;

EPOXIDATION; ETHYLENE; MECHANISMS; MOLYBDENUM; QUANTUM CHEMISTRY;

MOLYBDENUM COMPOUNDS;

EID: 84887042162     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.05.004     Document Type: Article

References (42)

1. F. Cavani, and J.H. Teles ChemSusChem 2 2009 508 534
2. Catalysts for Fine Chemical Synthesis Regio- and Stereocontrolled Oxidations and Reductions 2007 John Wiley Sons, Ltd. England
3. T.A. Nijhuis, M. Makkee, J.A. Moulijn, and B.M. Weckhuysen Ind. Eng. Chem. Res. 45 2006 3447 3459
4. S.A. Hauser, M. Cokoja, and F.E. Kuhn Catal. Sci. Technol. 3 2013 552 561
5. P.G. Cozzi Chem. Soc. Rev. 33 2004 410 421
6. P. Altmann, M. Cokoja, and F.E. Kühn Eur. J. Inorg. Chem. 2012 2012 3235 3239
7. W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel, and H. Glas J. Organomet. Chem. 555 1998 293 295
8. T. Michel, D. Betz, M. Cokoja, V. Sieber, and F.E. Kühn J. Mol. Catal. A Chem. 340 2011 9 14
9. H.-J. Lee, T.-P. Shi, D.H. Busch, and B. Subramaniam Chem. Eng. Sci. 62 2007 7282 7289
10. J.H. Espenson Chem. Commun. 0 1999 479 488
11. J.J. Haider, R.M. Kratzer, W.A. Herrmann, J. Zhao, and F.E. Kühn J. Organomet. Chem. 689 2004 3735 3740
12. J. Kollar, Catalytic Epoxidation of an Olefinically Unsaturated, Compound Using an Organic Hydroperoxide as an Epoxidizing, Agent, Halcon International, Inc., U.S. Patent 3,350,422, 1967; 85 J. Kollar, Epoxidation process, Halcon International, Inc., U.S. Patent 3,351,635, 1967; M.N. Sheng and J.G. Zajacek, Method of Producing Epoxides; The Atlantic Richfield Company, G.B. Patent 1,136,923, 1968.
13. F.E. Kühn, A.M. Santos, A.D. Lopes, I.S. Goncalves, E. Herdtweck, and C.C. Romao J. Mol. Cat. A Chem. 164 2000 25 38
14. F.E. Kühn, A.D. Lopes, A.M. Santos, E. Herdtweck, J.J. Haider, C.C. Romao, and A.G. Santos J. Mol. Catal. A Chem. 151 2000 147 160
15. F.E. Kühn, M. Groarke, É. Bencze, E. Herdtweck, A. Prazeres, A.M. Santos, M.J. Calhorda, C.C. Romão, I.S. Gonçalves, A.D. Lopes, and M. Pillinger Chem. Eur. J. 8 2002 2370 2383
16. A.A. Valente, Z. Petrovski, L.C. Branco, C.A.M. Afonso, M. Pillinger, A.D. Lopes, C.C. Romao, C.D. Nunes, and I.S. Goncalves J. Mol. Catal. A Chem. 218 2004 5 11
17. A. Al-Ajlouni, A.A. Valente, C.D. Nunes, M. Pillinger, A.M. Santos, J. Zhao, C.C. Romão, I.S. Gonçalves, and F.E. Kühn Eur. J. Inorg. Chem. 2005 2005 1716 1723
18. A. Günyar, and F.E. Kühn J. Mol. Catal. A Chem. 319 2010 108 113
19. M. Abrantes, A.M. Santos, J. Mink, F.E. Kuehn, and C.C. Romao Organometallics 22 2003 2112 2118
20. J. Zhao, A.M. Santos, E. Herdtweck, and F.E. Kuehn J. Mol. Catal. A Chem. 222 2004 265 271
21. C. Freund, M. Abrantes, and F.E. Kuehn J. Organomet. Chem. 691 2006 3718 3729
22. A.M. Al-Ajlouni, D. Veljanovski, A. Capape, J. Zhao, E. Herdtweck, M.J. Calhorda, and F.E. Kuehn Organometallics 28 2009 639 645
23. A. Capape, A. Raith, and F.E. Kuehn Adv. Synth. Catal. 351 2009 66 70
24. A. Capape, A. Raith, E. Herdtweck, M. Cokoja, and F.E. Kuehn Adv. Synth. Catal. 352 2010 547 556
25. D. Betz, A. Raith, M. Cokoja, and F.E. Kühn ChemSusChem 3 2010 559 562
26. P. Chaumette, H. Mimoun, L. Saussine, J. Fischer, and A. Mitschler J. Organomet. Chem. 250 1983 291 310
27. A.O. Chong, and K.B. Sharpless J. Org. Chem. 42 1977 1587 1590
28. P.J. Costa, M.J. Calhorda, and F.E. Kuhn Organometallics 29 2010 303 311
29. P.J. Costa, M.J. Calhorda, and F.E. Kuehn Organometallics 29 2009 303 311
30. A. Comas-Vives, A. Lledos, and R. Poli Chem. Eur. J. 16 2010 2147 2158
31. W.R. Thiel, and J. Eppinger Chem. Eur. J. 3 1997 696 705
32. P. Chandra, S.L. Pandhare, S.B. Umbarkar, M.K. Dongare, and K. Vanka Chem. Eur. J. 19 2013 2030 2040
33. L.F. Veiros, C.A. Gamelas, M.J. Calhorda, and C.C. Romao Organometallics 30 2011 1454 1465
34. S.A. Hauser, M. Cokoja, M. Drees, and F.E. Kuehn J. Mol. Catal. A Chem. 363-364 2012 237 244
35. H.B. Schlegel J. Comp. Chem. 3 1982 214 218
36. S.H. Vosko, L. Wilk, and M. Nusair Can. J. Phys. 58 1980 1200 1211
37. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B Condens. Matter 37 1988 785 789
38. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
39. P.C. Hariharan, and J.A. Pople Chem. Phys. Lett. 16 1972 217 219
40. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257 2261
41. A. Bergner, M. Dolg, W. Kuechle, H. Stoll, and H. Preuss Mol. Phys. 80 1993 1431 1441
42. L.J. Goossen, D. Koley, H.L. Hermann, and W. Thiel Organometallics 25 2006 54 67