Manganese (III) acetate dihydrate catalyzed aerobic epoxidation of unfunctionalized olefins in fluorous solvents

Tetrahedron

Volumn 54, Issue 26, 1998, Pages 7457-7464

  Ravikumar, K S ^a   Barbier, Francis ^a   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Catalysts; Epoxidation; Oxidation; Solvents and solvent effects

Indexed keywords

HEXAFLUORO 2 PROPANOL; LIMONENE; MANGANESE DERIVATIVE; PERFLUORO 2 BUTYLTETRAHYDROFURAN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; EPOXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032565899     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00396-2     Document Type: Article

References (29)

1. 1. Smith, J.G. Synthesis, 1984, 629.
2. 2. Bartok, M.; Lang, K.L: The chemistry of ethers, crown ethers hydroxyl groups and their sulphur analogues. In: Patai, S, editors. The Chemistry of Functional Groups. John Wiley & Sons, 1980: Part 2, Ch 14, p 609.
3. 3. Mukaiyama, T. Aldrichimica Acta, 1996, 29, 59.
4. 4. Mukaiyama, T.; Yamada, T. Bull. Chem. Soc. Jpn., 1995, 68, 17.
5. 5. Brodbelt, J.; Maleknia, S.; Liou, C. -C.; Lagow, R. J. Am. Chem. Soc., 1991, 113, 5913.
6. 6. Brodbelt, J.; Maleknia, S.; Lagow, R.; Lin, T. Y. J. Chem. Soc., Chem. Commun., 1991, 1705.
7. 7. Studer, A.; Jeger, P.; Wipf, P.; Curran, D.P. J. Org. Chem., 1997, 62, 2917 and references cited therein.
8. 8. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S. -Y.; Jeger, P.; Wipf, P.; Curran, D.P. Science, 1997, 275, 823.
9. 9. Klement, I.; Lutjens, H.; Knochel, P. Angew. Chem. Int. Ed. Engl. 1997, 36, 1454.
10. 10. Pozzi, G.; Banfi, S.; Manfredi, A.; Montanari, F.; Quici, S. Tetrahedron, 1996, 52, 11879.
11. 11. Sharpless, K.B.; Verhoeven, T.R. Aldrichimica Acta, 1979, 12, 63.
12. 12. Jorgensen, K.A. Chem. Rev., 1989 , 89, 431.
13. 13. Yamada, T.; Imagawa, K.; Mukaiyama, T. Chem. Lett., 1992, 2109.
14. 14 Groves, J.T.; Quinn, R.J. J. Am. Chem. Soc., 1985, 107, 5790.
15. 15. Kesavan, V.; Chandrasekaran, S. J. Chem. Soc., Perkin Trans. 1, 1997, 3115.
16. 16. Melikyan, G.G. Synthesis, 1993, 833.
17. 17. Snider, B.B., Merritt, J.E.; Dombroski, M.A.; Buckman, B.O. J. Org. Chem., 1991, 56, 5544.
18. 18. Snider, B.B.; Patricia, J.J.; Kates, S.A. J. Org. Chem., 1988, 53, 2137.
19. 19. When methyljasmonate was allowed to react with our reagent system, the starting cis-olefin was recovered unchanged
20. 20. Kaneda, K.; Haruna, S.; Imanaka, T.; Hamamoto, M.; Nishiyama, Y.; Ishi, Y. Tetrahedron Lett., 1992, 33, 6827.
21. 21. Pozzi, G.; Montanari, F.; Rispens, M.T. Synth. Commun., 1997, 27, 447
22. 22. Nam, W.; Kim, H.J..; Kim, S.H.; Ho, R.Y.N.; Valentine, J.S. Inorg. Chem., 1996, 35, 1045.
23. 23. Gonsalves, A.M.R.; Pereira, M.M.; Serra, A.C.; Johnstone, R.A.W.; Nunes, M.L.P.G. J. Chem. Soc., Perkin Trans 1, 1994, 2053.
24. 24. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Tetrahedron, 1996, 52, 4593.
25. 25. Battioni, P.; Renaud, J.P.; Bartoli, J.F.; Reina-Artiles, M.; Fort, M.; Mansuy, D. J. Am., Chem., Soc., 1988, 110, 8462.
26. 26. Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H. Tetrahedron, 1994, 50, 3663.
27. 27. Cross, A.D. J. Am. Chem. Soc., 1962, 84, 3206.
28. 28. Carman, R.M.; Klika, K.D. Aust. J. Chem., 1991, 44, 1803.
29. 29. Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. Tetrahedron, 1994, 50, 10539.