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Efficient olefin epoxidation with tetrabutylammonium periodate catalyzed by manganese porphyrin in the presence of imidazole

โœ Scribed by Daryoush Mohajer; Shahram Tangestaninejad

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
244 KB
Volume
35
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Epoxidation of various olefins is achieved by

Mm-n-butylammarium periodate in the. preamce of manganese (III) meso-tetraphenylporphyrin and imidamle in CH$l,. with high selectivity and yield under mild conditions. The modeling of cytochrome P-450 class of enzymes with synthetic metalloporphyrin complexes accompanied by various oxygen sources, for oxyfunctionalization of hydrocarbons, has received the immense attention of different research groups for over a decade '. Considerable effort has been aimed at introducing new catalytic systems with higher degree of chemo-and stereoselectivity and with greater stability under oxidizing conditions'. Recently, it was demsonstrated that NaIO, can be employed as an effective oxygen atom donor for the epoxidation of olefins, catalyzed by [ MnXII(TPP)(Cl)] (TPP--meso-tetraphenylporphyrin) in a two-phase medium'.

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Oxidation of hydrocarbons, into their corresponding epoxide, alcohol and/or ketone, was achieved with tetrabutylammonium monopersulfate in the presence of manganese(III) meso-tetraphenylporphyrin catalyst and axial imidazole ligand in CH 2 Cl 2 in low to very high yields (13-100%) and good to excell

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Several remarkable selectivities in competitive epoxidations using a ruthenium porphyrin / 2,6-disubstituted pyridine N-oxide system were observed. The pro fp sal that the active intermediate of this system differed from the trarrsdioxo complex of ruthenium porp yrin was indicated. Much research ha