Selective epoxidation of (+)-limonene employing methyltrioxorhenium as catalyst

Journal of Molecular Catalysis A: Chemical

Volumn 358, Issue , 2012, Pages 159-165

  Michel, Typhne ^a   Cokoja, Mirza ^a   Sieber, Volker ^a   Kühn, Fritz E ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

1,2 Limonene oxide; Epoxidation; Homogeneous catalysis; Methyltrioxorhenium; N Base adduct; Terpenes

Indexed keywords

BIPYRIDINES; HOMOGENEOUS CATALYSIS; METHYLTRIOXORHENIUM; MOLAR RATIO; N-BASE ADDUCT; OPTIMAL CONDITIONS; PYRAZOLES; SELECTIVE EPOXIDATION; TERPENES;

CATALYSTS; DICHLOROMETHANE; EPOXIDATION; OLEFINS; REACTION KINETICS; UREA;

RHENIUM COMPOUNDS;

EID: 84860277575     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2012.03.011     Document Type: Article

References (44)

1. P. Gallezot Catal. Today 121 2007 76 91
2. C. Fischer Food Flavors: Biology and Chemistry 1997 The Royal Society of Chemistry United Kingdom
3. C.S. Sell The Chemistry of Fragrance: From Perfumer to Consumer 2nd ed. 2006 The Royal Society of Chemistry United Kingdom
4. Q.H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Li, and K.-X. Su Chem. Rev. 105 2005 1603 1662
5. N. Mizuno, K. Yamaguchi, and K. Kamata Coord. Chem. Rev. 249 2005 1944 1956
6. M. Blair, P.C. Andrews, B.H. Fraser, C.M. Forsyth, P.C. Junk, M. Massi, and K.L. Tuck Synthesis 10 2007 1523 1527
7. C.M. Byrne, S.D. Allen, E.B. Lobkovsky, and G.W. Coates J. Am. Chem. Soc. 126 2004 11404 11405
8. T. Kellersohn Ullmann's Encyclopedia of Industrial Chemistry 6th ed. 1998 Wiley-VCG New-York
9. A. Bordoloi, F. Lefebvre, and S.B. Halligudi J. Mol. Catal. A: Chem. 270 2007 177 184
10. T. Michel, D. Betz, M. Cokoja, V. Sieber, and F.E. Kühn J. Mol. Catal. A: Chem. 340 2011 9 14
11. D. Mandelli, M.C.A.v. Vliet, R.A. Sheldon, and U. Schuchardt Appl. Catal. A 219 2001 209 213
12. N.K.K. Raj, V.G. Puranik, C. Gopinathan, and A.V. Ramaswamy Appl. Catal. A 256 2003 265 273
13. M.J.d. Silva, P. Robles-Dutenhefner, L. Menini, and E.V. Gusevskaya J. Mol. Catal. A: Chem. 201 2003 71 77
14. A. Asouti, and L.P. Hadjiarapoglou Synlett 12 2001 1847 1850
15. M. Caovilla, A. Coavilla, S.B.C. Pergher, M.C. Esmelindro, C. Fernandes, C. Dariva, K. Bernardo-Gusmão, E.G. Oestreicher, and O.A.C. Antunes Catal. Today 133-135 2008 695 698
16. L. Saikia, D. Srinivas, and P. Ratnasamy Appl. Catal. A 309 2006 144 154
17. L. Saikia, and D. Srinivas Catal. Today 141 2009 66 71
18. K.S. Ravikumar, F. Barbier, J.-P. Bégué, and D. Bonnet-Delpon Tetrahedron 54 1998 7457 7464
19. M. Abrantes, P. Neves, M.M. Antumes, S. Gago, F.A.A. Paz, A.E. Rodrigues, M. Pillinger, I.S. Gonalves, C.M. Silva, and A.A. Valente J. Mol. Catal. A: Chem. 320 2010 19 26
20. L. Salles, J.-M. Brégeault, and R. Thouvenot C.R. Acad. Sci. Paris, Sériee IIc, Chimie/Chemistry 3 2000 183 187
21. R. Saladino, A. Andreoni, V. Neri, and C. Crestini Tetrahedron 61 2005 1069 1075
22. F.E. Kühn, A. Scherbaum, and W.A. Herrmann J. Organomet. Chem. 689 2004 4149 4164
23. F.E. Kühn, and W.A. Herrmann Structure and Bonding vol. 97 2000 Springer Verlag Germany
24. S. Yamazaki Organic Biomol. Chem. 8 2010 2377 2385
25. H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault, and A. Deloffre J. Mol. Catal. A: Chem. 133 1998 255 265
26. R. Saladino, M.C. Ginnasi, D. Collalto, R. Bernini, and C. Crestini Adv. Synth. Catal. 352 2010 1284 1290
27. W.A. Herrmann, A.M.J. Rost, J.K.M. Mitterpleininger, N. Szesni, S. Sturm, R.W. Fischer, and F.E. Kühn Angew. Chem. Int. Ed. 46 2007 7301 7303
28. P. Ferreira, W.-M. Xue, E. Bencze, E. Herdtweck, and F.E. Kühn Inorg. Chem. 40 2001 5834 5841
29. F.E. Kühn, A.M. Santos, P.W. Roesky, E. Herdtweck, W. Scherer, P. Gisdakis, I.V. Yudanov, C.D. Valentin, and N. Rösch Chem. Eur. J. 5 1999 3603 3615
30. M.-D. Zhou, J. Zhao, J. Li, S. Yue, C.-N. Bao, J. Mink, S.-L. Zang, and F.E. Kühn Chem. Eur. J. 13 2007 158 166
31. M.-D. Zhou, Y. Yu, A. Capapé, K.R. Jain, E. Herdtweck, X.-R. Li, J. Li, S.-L. Zang, and F.E. Kühn Chem. Asian J. 4 2009 411 418
32. M.-D. Zhou, S.-L. Zang, E. Herdtweck, and F.E. Kühn J. Organomet. Chem. 693 2008 2473 2477
33. A. Capapé, M.-D. Zhou, S.-L. Zang, and F.E. Kühn J. Organomet. Chem. 693 2008 3240 3244
34. P. Altmann, and F.E. Kühn J. Organomet. Chem. 694 2009 4032 4035
35. W. Adam, and C.M. Mitchell Angew. Chem. Int. Ed. 35 1996 533 535
36. T.R. Boehlow, and C.D. Spilling Tetrahedron Lett. 37 1996 2717 2720
37. C.C. Romão, F.E. Kühn, and W.A. Herrmann Chem. Rev. 97 1997 3197 3246
38. J. Rudolph, K.L. Reddy, J.P. Chiang, and K.B. Sharpless J. Am. Chem. Soc. 119 1997 6189 6190
39. C. Copéret, H. Adolfsson, and K.B. Sharpless Chem. Commun. 1997 1565 1566
40. W.A. Herrmann, H. Ding, R.M. Kratzer, F.E. Kühn, J.J. Haider, and R.W. Fischer J. Organomet. Chem. 549 1997 319 322
41. W.A. Herrmann, R.M. Kratzer, H. Ding, W.R. Thiel, and H. Glas J. Organomet. Chem. 555 1998 293 295
42. S.M. Nabavizadeh, A. Akbari, and M. Rashidi Dalton Trans. 2005 2423 2427
43. H. Wynberg, and B. Greijdanus J. Chem. Soc., Chem. Commun. 1978 427 428
44. W.-D. Wang, and J.H. Espenson J. Am. Chem. Soc. 120 1998 11335 11341