Selective oxidation of vinyl ethers and silyl enol ethers with hydrogen peroxide catalyzed by peroxotungstophosphate

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7174-7177

  Yamamoto, Hiroyo ^a   Tsuda, Masaya ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROMETHANE; ETHER DERIVATIVE; HEPTANE; HYDROGEN PEROXIDE; HYDROXYALDEHYDE; KETONE DERIVATIVE; METHANOL; OCTANE; PHOSPHOTUNGSTIC ACID; SILANE DERIVATIVE; SOLVENT; VINYL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION;

EID: 0030829196     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970440h     Document Type: Article

References (43)

1. Rapp, R. D.; Borowitz, I. J. J. Chem. Soc., Chem. Commun. 1969, 1202.
2. Piancatelli, G.; Scettri, A.; D'Auria, M. Tetrahedron Lett. 1977, 3483.
3. Troisi, L.; Cassidei, L.; Lopez, L.; Mello, R.; Curci, R. Tetrahedron Lett. 1989, 30, 257.
4. (a) Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 4319.
5. (b) Hassner, A.; Reuss, R.; Pinnick, H. W. J. Org. Chem. 1975, 40, 3427.
6. Rubottom, G. M.; Gruber, J. M.; Mong, G. M. J. Org. Chem. 1976, 41, 1673.
7. McCormick, J. P.; Tomasik, W.; Johnson, M. W. Tetrahedron Lett. 1981, 22, 607.
8. Kaneda, K.; Kii, N.; Jitsukawa, K.; Teranishi, S. Tetrahedron Lett. 1981, 22, 2595.
9. Jefford, C. W.; Kohmoto, S.; Boukouvalas, J.; Burger, U. J. Am. Chem. Soc. 1983, 105, 6498.
10. Oppolzer, W.; Dudfield, P. Helv. Chem. Acta 1985, 68, 216.
11. Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954.
12. (a) Takai, T.; Yamada, T.; Rhode, O.; Mukaiyama, T. Chem. Lett. 1991, 281.
13. (b) Yorozu, K.; Takai, T.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1994, 67, 2195.
14. (a) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172.
15. (b) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389.
16. (c) Adam, W.; Fell, R. T.; Mock-Knoblauch, C.; Saha-Möller, C. R. Tetrahedron Lett. 1996, 37, 6531.
17. Rozen, S.; Bareket, Y. J. Chem. Soc., Chem. Commun. 1996, 627.
18. Raju, S. V. N.; Upadhya, T. T.; Ponrathnam, S.; Daniel, T.; Sudalai, A. J. Chem. Soc., Chem. Commun. 1996, 1969.
19. Iriuchijima, S.; Maniwa, K.; Tsuchihashi, G. J. Am. Chem. Soc. 1974, 96, 4280.
20. (a) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. J. Org. Chem. 1988, 53, 3587.
21. (b) Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1996, 61, 5307.
22. Sakaguchi, S.; Watase, S.; Katayama, Y.; Sakata, Y.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 5681.
23. Ishii, Y.; Sakata, Y. J. Org. Chem. 1990, 55, 5545.
24. (e) Sakata, Y.; Ishii, Y. J. Org. Chem. 1991, 56, 2633.
25. (f) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 1523.
26. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075.
27. (a) Ogura, K.; Tsuchihashi, G. Tetrahedron Lett. 1972, 2681.
28. (b) Ogura, K.; Furukawa, S.; Tichihashi, G. Chem. Lett. 1974, 659.
29. Balanson, R. D.; Kobal, V. M.; Schumaker, R. R. J. Org. Chem. 1977, 42, 393.
30. Oldenziel, O. H.; Leusen, A. M. Tetrahedron Lett. 1974, 167.
31. (a) Seki, Y.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1978, 17, 119.
32. (b) Murai, S.; Kato, T.; Sonoda, N.; Seki, Y.; Kawamoto K. Ibid. 1979, 18, 393.
33. Matsukawa, M.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 5877.
34. (a) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605.
35. (b) Kanemoto, S.; Oshima, K.; Matsubara, S.: Takai, K.; Nozaki, H. Ibid. 1983, 24, 2185.
36. (c) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462.
37. (d) Einhorn, J.; Einhron, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452.
38. (a) Hurd, C. D.; Saunders, W. H. Jr. J. Org. Chem. 1952, 74, 5324.
39. (b) Russell, G. A.; Ochryowycz, L. A. J. Org. Chem. 1969, 34, 3618.
40. Creavy, X.; Rollin, A. J. J. Org. Chem. 1977, 42, 4231.
41. House, H. O.; Czuba, L. L.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.
42. Normant, J. F.; Commercon, A.; Bourgain, M.; Villiras, J. Tetrahedron Lett. 1975, 3833.
43. Morris, P. E., Jr.; Kiely, D. E. J. Org. Chem. 1987, 52, 1149.