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 (CH2CI2–H2O) medium at 24 ± 2 °C.
References
1.
(a) McMurryT. J., and GrovesJ. T., Cytochrome P-450: Mechanism and Biochemistry, ed. Ortiz de MontellanoP. R., 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) ArasasinghamR. D., HeG. X., and BruiceT. C., 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.
MohajerD., and TangestaninejadS., J. Chem. Soc., Chem. Commun., 1993, 240.
4.
(a) CrovesJ. T., and NemoT. E., 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.
RodgersK. R., and GoffH. M., 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.
GrovesJ. T., KruperW. J.Jr, and HaushalterR. C., J. Am. Chem. Soc., 1980, 102, 6375.
7.
(a) MontanariF., BanfiS., and QuiciS., 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.
