Kinetic studies of olefin epoxidation with hydrogen peroxide in 1,1,1,3,3,3-hexafluoro-2-propanol reveal a crucial catalytic role for solvent clusters

Advanced Synthesis and Catalysis

Volumn 346, Issue 2-3, 2004, Pages 275-280

  Berkessel, Albrecht ^a   Adrio, Jens A ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Arsonic acids; Epoxidation; Fluorinated alcohols; Hydrogen peroxide; Kinetics; Solvent clusters

Indexed keywords

ALCOHOL; ALKENE; ARSONIC ACID DERIVATIVE; HYDROGEN PEROXIDE; PROPANOL;

ACCELERATION; ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CONCENTRATION (PARAMETERS); DATA ANALYSIS; ENZYME MECHANISM; EPOXIDATION; OXIDATION KINETICS; REACTION ANALYSIS;

EID: 1942471011     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303222     Document Type: Article

References (19)

1. R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986.
2. K. Neimann, R. Neumann, Org. Lett. 2000, 2, 2861-2863.
3. M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, Synlett 2001, 248-250.
4. K. S. Ravikumar, J.-P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 1998, 39, 3141-3144.
5. G.-J. ten Brink, B. C. M. Fernandes, M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, J. Chem. Soc. Perkin Trans. 1 2001, 224-228.
6. M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, J. Chem. Soc. Perkin Trans. 1 2000, 377-380.
7. M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, Tetrahedron Lett. 1999, 40, 5239-5242.
8. A. Berkessel, M. R. M. Andreae, Tetrahedron Lett. 2001, 42, 2293-2295.
9. S. P. de Visser, J. Kaneti, R. Neumann, S. Shaik, J. Org. Chem. 2003, 68, 2903-2912.
10. 2 which takes place effectively in fluorinated alcohols: ref. [11]
11. R. Ben-Daniel, S. P. de Visser, S. Shaik, R. Neumann, J. Am. Chem. Soc. 2003, 125, 12116-12117.
12. total ≥ 0.5). No additional distinct kinetic regimes could be detected.
13. S. E. Jacobson, F. Mares, P. M. Zambri, J. Am. Chem. Soc. 1979, 101, 6946-6950.
14. - (6) = 351; see ref.[15]
15. B. Megido-Almaraz; dissertation, University of Cologne, 2003.
16. A. Berkessel, J. A. Adrio, to be published elsewhere.
17. M. Fioroni, K. Burger, A. E. Mark, D. Roccatano, J. Phys. Chem. B 2001, 105, 10967-10975.
18. D.-P. Hong, M. Hoshino, R. Kuboi, Y. Goto, J. Am. Chem. Soc. 1999, 121, 8427-8433.
19. H. Schaal, T. Häber, M. A. Suhm, J. Phys. Chem. A 2000, 104, 265-274.