Comparison of amine additives most effective in the new methyltrioxorhenium-catalyzed epoxidation process

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 3991-3994

  Adolfsson, Hans ^a   Converso, Antonella ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC AMINE; HYDROGEN PEROXIDE; METAL DERIVATIVE; METHYLTRIOXORHENIUM; NICOTINONITRILE; PYRAZOLE; PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; EPOXIDATION; REACTION ANALYSIS;

EID: 0033591184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00661-9     Document Type: Article

References (25)

1. [1] Oxidation processes catalyzed by MTO: olefins; a) Hoechst AG; Herrmann, W. A.; Marz, D. W.; Kuchler, J. G.; Weichselbaumer, G.; Fischer, R. W.; DE 3.902.357, 1989.
2. b) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. 1991, 703, 1706; Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
3. b) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. 1991, 703, 1706; Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
4. c) Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243.
5. d) ARCO Chemical Technology; Crocco, G. L.; Shum, W. P.; Zajacek, J. G.; Kesling, H. S., Jr.; US 5.166.372, 1992. amines;
6. e) Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Tetrahedron Lett. 1995, 36, 6415;
7. f) Zhu, Z.; Espenson J. H. J. Org. Chem. 1995, 60, 1326;
8. g) Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Tetrahedron Lett. 1996, 37, 805;
9. h) Goti, A.; Nannelli, L. Tetrahedron Lett. 1996, 37, 6025;
10. i) Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. J. Org. Chem. 1996, 61, 8099;
11. j) Yamazaki, S. Bull. Soc. Chem. Jpn. 1997, 70, 877;
12. k) Coperét, C.; Adolfsson, H.; Khuong, T.-A. V.; Yudin, A. K.; Sharpless, K. B. J. Org. Chem. 1998, 63, 1742. sulphides;
13. l) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121.
14. m) Vasell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491. phosphines;
15. n) Abu-Omar, M. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 777, 272. alkynes;
16. o) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7728. phenols;
17. p) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R. J. Org. Chem. 1994, 59, 8281. arenes;
18. q) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R. Fisher, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475. oxygen insertion in C-H bonds; see 11e; Baeyer-Villiger oxidation;
19. r) Herrmann, W. A.; Fischer, R. W.; Correia, J. D. G. J. Mol. Cat. 1994, 94, 213.
20. [2] a) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 779, 6189.
21. b) Copéret, C.; Adolfsson, H.; Sharpless, K. B. Chem. Commun. 1997, 16, 1565.
22. [3] Herrmann, W. A.; Kratzer, R. M.; Ding, H.; Thiel, W. R.; Glas, H. J. Organomet. Chem. 1998, 555, 293.
23. [4] Epoxidations using pyrazoles in place of pyridines are also described in the Scripps Research Institute U.S. Patent Application Serial# 08/842,732.
24. [5] A full paper on the use of the 3-cyanopyridine additive in MTO-catalyzed epoxidations is in preparation
25. 4 (s) and the solvent is removed under reduced pressure. The crude epoxide is purified by vacuum distillation to yield 7.58 g (87%).