A heterogeneous tungsten catalyst for epoxidation of terpenes and tungsten-catalyzed synthesis of acid-sensitive terpene epoxides

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7267-7270

  Villa de P , Aída L ^a   Sels, Bert F ^a   De Vos, Dirk E ^a   Jacobs, Pierre A ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; TERPENE DERIVATIVE; TUNGSTEN;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPOXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033578953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990790z     Document Type: Article

References (35)

1. Bauer, K.; Garbe, D.; Surburg, H. Common Fragrance and Flavor Materials; Wiley-VCH: New York, 1997.
2. Fehr, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2407.
3. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
4. Ullmann's Encyclopedia of Industrial Chemistry, 6th Ed., Electronic Release; Wiley-VCH: New York, 1998.
5. (a) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
6. (b) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553.
7. (c) Venturello, C.; D'Aloisio, R.; Bart, J. C. J.; Ricci, M. J. Mol. Catal. 1985, 32, 107.
8. (a) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, Y.; Ogawa, M. J. Org. Chem. 1988, 53, 3587.
9. (b) Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1996, 61, 5307.
10. Duncan, D. C.; Chambers, R. C.; Hecht, E.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 681.
11. Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252.
12. (a) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Panyella, D.; Noyori, R. Bull. Chem. Soc. Jpn. 1997, 70, 905.
13. (b) Sato, K.; Aoki, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1998, 61, 8310.
14. Prandi, J.; Kagan, H. B.; Mimoun, H. Tetrahedron Lett. 1986, 27, 2617.
15. (a) Clerici, M. G.; Ingallina, P. J. Catal. 1993, 140, 71.
16. (b) Blasco, T.; Corma, A.; Navarro, M. T.; Pérez Pariente, J. J. Catal. 1995, 156, 65.
17. (a) Prat, D.; Delpech, B.; Lett, R. Tetrahedron Lett. 1986, 27, 711.
18. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386.
19. (c) Neumann, R.; Khenkin, A.; Juwiler, D.; Miller, H.; Gara, M. J. Mol. Catal. 1997, 117, 159.
20. (d) Venturello, C.; Gambaro, M. J. Org. Chem. 1991, 56, 5924.
21. (a) Battioni, P.; Renaud, J. P.; Bartoli, J. F.; Reina-Artiles, M.; Fort, M.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8462.
22. (b) De Vos, D. E.; Sels, B.; Reynaers, M.; Subba Rao, Y. V.; Jacobs, P. A. Tetrahedron Lett. 1998, 39, 3221.
23. (a) Villa, A. L.; De Vos, D. E.; Montes, C.; Jacobs, P. A. Tetrahedron Lett. 1998.
24. (b) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
25. (c) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189.
26. (d) Yudin, A. K.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 11536.
27. (e) Copéret, C.; Adolffson, H.; Sharpless, K. B. Chem. Commun. 1997, 1565.
28. (f) Rudler, H.; Gregorio, J. R.; Denise, B.; Brégeault, J. M.; Deloffre, A. J. Mol. Catal. 1998, 133, 255.
29. 1H FT NMR spectra; Aldrich Chemical Co.: Milwaukee, 1993.
30. Fdil, N.; Romane, A.; Allaoud, S.; Karim, A.; Castanet, Y.; Mortreux, A. J. Mol. Catal. 1996, 108, 15.
31. Boyd, D. R.; Sharma, N. D.; Smith, A. E. J. Chem. Soc., Perkin Trans. 1 1982, 2767.
32. Takai, T.; Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1991, 64, 2513.
33. Li, W.; Li, Y.; Li, Y. J. Chin, Chem. Soc. 1995, 42, 701.
34. Ray, N. C.; Raveendranath, P. C.; Spencer, T. A. Tetrahedron 1992, 48, 9427.
35. Van Hijfte, L.; Kolb, M. Tetrahedron 1992, 48, 6393.