Sodium Periodate Epoxidation of Alkenes Catalysed by Manganese Porphyrins

Abstract

Epoxidation of alkenes with different electronic and steric properties has been performed with high selectivity by sodium periodate in the presence of acetatotetraarylporphinatomanganese(III) complexes containing electron releasing or withdrawing groups at the ortho positions of the aryl rings, in a two-phase (CH₂Cl₂–H₂O) medium at 24±2°C.

References

1. (a) T. J. McMurry and J. T. Groves, Cytochrome P-450: Mechanism and Biochemistry, ed. P. R. Ortiz de Montellano, Plenum Press, New York and London, 1986, ch. 1; (b) D. Mansuy, Coord. Chem. Rev., 1993, 125, 129; (c) B. Meunier, Chem. Rev., 1992, 92, 1411; (d) I. Tabushi, Coord. Chem. Rev., 1988, 86, 1; (e) D. Dolphin, T. G. Traylor and L. Y. Xie, Acc. Chem. Res., 1997, 30, 251; (f) A. Maldotti, A. Molinari, P. Bergamini, R. Amadelli and D. Mansuy, J. Mol. Catal., 1996, 113, 147; (g) P. Bhyrappa, J. K. Young, J. S. Moore and K. S. Suslick, J. Mol. Catal., 1996, 113, 109.
2. (a) R. D. Arasasingham, G. X. He and T. C. Bruice, J. Am. Chem. Soc., 1993, 115, 7985; (b) P. Battioni, J. P. Renaud, J. F. Bartoli, M. Reins-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc., 1988, 110, 8462; (c) A. Robert and B. Meunier, New. J. Chem., 1988, 12, 885; (d) J. P. Collman, J. I. Brauman, B. Meunier, T. Hayashi, T. Kodadek and S. A. Raybuck, J. Am. Chem. Soc., 1985, 107, 2000; (e) B. de Poorter and B. Meunier, J. Chem. Soc., Perkin Trans. 2, 1985, 1735; (f) J. R. Lindsay-Smith and P. R. Sleath, J. Chem. Soc., Perkin Trans. 2, 1982, 1009; (g) J. T. Groves, T. E. Nemo and R. S. Myers, J. Am. Chem. Soc., 1979, 101, 1032.
3. D. Mohajer and S. Tangestaninejad, J. Chem. Soc., Chem. Commun., 1993, 240.
4. (a) J. T. Croves and T. E. Nemo, J. Am. Chem. Soc., 1983, 105, 5786; (b) D. Ostovic and T. C. Bruice, Acc. Chem. Res., 1992, 25, 314; (c) D. Ostovic and T. C. Bruice, Am. Chem. Soc., 1989, 111, 6511.
5. (a) K. R. Rodgers and H. M. Goff, J. Am. Chem. Soc., 1988, 110, 7049; (b) D. Mansuy, P. Battioni and J. P. Renaud, J. Chem. Soc., Chem. Commun., 1984, 1255; (c) R. W. Lee, P. C. Nakagaki and T. C. Bruice, J. Am. Chem. Soc., 1989, 111, 1368.
6. J. T. Groves, W. J. Kruper Jr and R. C. Haushalter, J. Am. Chem. Soc., 1980, 102, 6375.
7. (a) F. Montanari, S. Banfi and S. Quici, Pure Appl. Chem., 1989, 61, 1631; (b) J. A. S. Razenberg, R. J. M. Notle and W. Drenth, Tetrahedron Lett., 1984, 25, 789; (c) A. W. van der Made, J. W. H. Smeets, R. J. M. Nolte and W. Drenth, J. Chem. Soc., Chem. Commun., 1983, 1204.