ChemInform Abstract: Effect of pH on the Epoxidation of Alkenes by the Cytochrome P-450 Model Manganese(III) Porphyrin/Hypochlorite

ChemInform ◽  
1989 ◽  
Vol 20 (37) ◽  
Author(s):  
A. W. VAN DER MADE ◽  
J. M. C. BAX ◽  
R. J. M. NOLTE ◽  
W. DRENTH
Keyword(s):  
Effect Of Ph ◽  
Epoxidation Of Alkenes ◽  
Cytochrome P 450

scholarly journals Effect of pH on the epoxidation of alkenes by the cytochrome P-450 model manganese(III) porphyrin/hypochlorite

1989 ◽  
Vol 108 (5) ◽  
pp. 185-188 ◽  
Author(s):  
A. W. van der Made ◽  
J. M. C. Bax ◽  
R. J. M. Nolte ◽  
W. Drenth
Keyword(s):  
Effect Of Ph ◽  
Epoxidation Of Alkenes ◽  
Cytochrome P 450

Cytochrome P-450 model reaction: effects of substitution on the rate of aromatic hydroxylation

2000 ◽  
Vol 04 (03) ◽  
pp. 285-291 ◽  
Author(s):  
NASSER SAFARI ◽  
FARZAD BAHADORAN ◽  
MOHAMMAD REZA HOSEINZADEH ◽  
REZA GHIASI
Keyword(s):  
Relative Rate ◽  
Kinetic Method ◽  
Oxidation Reactions ◽  
Aromatic Rings ◽  
Aromatic Hydroxylation ◽  
Catalysed Oxidation ◽  
Epoxidation Of Alkenes ◽  
Cytochrome P 450 ◽  
Related Compounds ◽  
Electron Withdrawing Substituents

The study of haemin-catalysed oxidation reactions was extended to substituted aromatic rings. Both electron-donating and electron-withdrawing substituents on aromatic rings act as para- and meta-directing agents in the presence of tetrakis(2,6-dichlorophenyl)porphyrin iron(III) chloride as catalyst and m-chloroperbenzoic acid as oxidant. A new kinetic method for measuring relative rates of epoxidation of alkenes and related compounds has been developed; while steric hindrance results in decreasing the rate of hydroxylation, electron-rich and electron-withdrawing substituents were found to increase the rate of hydroxylation. A linear relationship between the logarithm of the relative rate of hydroxylation and σ Hammet is obtained, although electron-donating and electron-withdrawing substituents fit separate lines. Addition of pyridine to haemin was shown to increase the yield of epoxidation but decrease the yield of aromatic hydroxylation.

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