✍ Scribed by Nasser Safari; Farzad Bahadoran; Mohammad Reza Hoseinzadeh; Reza Ghiasi
No coin nor oath required. For personal study only.
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.
📜 SIMILAR VOLUMES
l a 16 Scheme 4. a) [BuLi. T H E 90 min, -78'C; BzCl, pyridine, 12h, 20-C; 5% Na/Hg. 5h. -20 C. 3 5 % : h) Bu,NE THF, 1 h, 0'C. 85%; c) tiBuLi. CICO,Et, THF, 1 h, ~ 30 C. 8 5 % ; d ) morpholine. THF. 2h, reflux; 60% CH,CO,H, 2h. 5 0 °C 75%; e) TBDPSCI. imidazole. DMF. ?d, -60 C, 9 6 % ; f) Ac,O, pyr
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