Catalytic Alkene Epoxidation with Hydrogen Peroxide in the Presence of 5,10,15,20-Tetrakis(2,6-dichloro-3-sulfonatophenyl)porphyrinatomanganese(III) Acetate and Imidazole

Abstract

Different alkene epoxidations were performed with aqueous hydrogen peroxide (35%) in MeCN with low to very high conversions and good to excellent selectivities by 5,10,15,20-tetrakis(2,6-dichloro-3-sulfonatophenyl)porphyrinatomanganese(III) acetate and imidazole at room temperature.

References

1. (a) R. A. Sheldon and J. K. Kochi, Metal Catalyzed Oxidation of Organic Compounds, Academic Press, New York, 1981; (b) F. Montanari, S. Banfi and S. Quici, Pure Appl. Chem., 1989, 61, 1631; (c) D. Mansuy, Pure Appl. Chem., 1990, 62, 741; (d) T. G. Traylor, Pure Appl. Chem., 1991, 63, 265; (e) B. Meunier, Chem. Rev., 1992, 92, 1411.
2. (a) V. Karunaratne and D. Dolphin, J. Chem. Soc., Chem. Commun., 1995, 2105; (b) S. M. S. Chauhan, P. P. Mohapatra, B. Kalra, T. S. Kohli and S. Satapathy, J. Mol. Catal., 1996, 113, 239; (c) D. Dolphin, T. G. Traylor and L. Y. Xie, Acc. Chem. Res., 1997, 30, 251 and references therein.
3. (a) R. Panicucci and T. C. Bruice, J. Am. Chem. Soc., 1990, 112, 6063; (b) T. C. Bruice, Acc. Chem. Res., 1991, 24, 243.
4. H. Turk and W. T. Ford, J. Org. Chem., 1991, 56, 1253.
5. S. Campestrini and B. Meunier, Inorg. Chem., 1992, 31, 1999.
6. M. A. Martinez-Lorente, P. Battioni, W. Kleemiss, J. F. Bartol and D. Mansuy, J. Mol. Catal., 1996, 113, 343.
7. A. J. Appleton, S. Evans and J. R. Lindsay Smith, J. Chem. Soc., Perkin Trans. 2, 1995, 281.
8. P. Battioni, J. P. Renaud, J. F. Bartoli, M. Reina-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc., 1988, 110, 8462.
9. G. B. Payne, P. H. Deming and P. H. Williams, J. Org. Chem., 1961, 26, 659.