Bipyridine N,N'-dioxide: A felicitous ligand for methyltrioxorhenium- catalyzed epoxidation of olefins with hydrogen peroxide

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 87-88

  Nakajima, Makoto ^a   Sasaki, Yuka ^a   Iwamoto, Hatsue ^a   Hashimoto, Shun Ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BIPYRIDINE DERIVATIVE; HYDROGEN PEROXIDE;

ARTICLE; CATALYSIS; EPOXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0031983770     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10495-6     Document Type: Article

References (17)

1. (a) Mijs, W.J.; deJonge, C.R.H.I. Organic Syntheses by Oxidation with Metal Compounds; Plenum Press: New York, 1986.
2. (b) Holm, R.H. Chem. Rev. 1987, 87, 1401-1449.
3. (c) Jørgensen, K.A. Chem. Rev. 1989, 89, 431-458.
4. (c) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
5. Mukaiyama T., Yamada T. Bull. Chem. Soc. Jpn. 58:1995;17-35. and references cited therein.
6. Sato K., Aoki M., Ogawa M., Hashimoto T., Panyella D., Noyori R. Bull. Chem. Soc. Jpn. 70:1997;905-915. and references cited therein.
7. For a review, see: Herrmann, W.A.; Kühn, F.E. Acc. Chem. Res. 1997, 30, 169-180.
8. (a) Herrmann, W.A.; Fischer, R.W.; Marz, D.W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641.
9. (b) Herrmann, W.A.; Fischer, R.W.; Scherer, W.; Rauch, M.U. Angew. Chem. Int. Ed. Engl. 1993, 32, 1157-1160.
10. (c) Herrmann, W.A.; Fischer, R.W.; Rauch, M.U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266.
11. 2, see: (a) Boehlow, T.R.; Spilling, C.D. Tetrahedron Lett. 1996, 37, 2717-2720.
12. (b) Adam, W.; Mitchell, C.M. Angew. Chem. Int. Ed. Engl. 1996, 35, 533-535.
13. (a) Rudolph, J.; Reddy, K.L.; Chiang, J.P.; Sharpless, K.B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
14. (b) Copéret, C.; Adolfsson, H.; Sharpless, K.B. Chem. Commun. 1997, 1565-1566.
15. Sharpless also observed N-oxidation of 3-cyanopyridine during MTO oxidation process. b.
16. Bipyridine N,N′-dioxide did not act as an oxidant in MTO-catalyzed epoxidation.
17. Nakajima M., Sasaki Y., Shiro M., Hashimoto S. Tetrahedron: Asymmetry. 8:1997;341-344.