Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 346, Issue 2-3, Pages 190-194Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200303204
Keywords
dihydroxylation; epoxidation; hydrogen peroxide; iron; N ligands; peracetic acid
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Iron complexes (tpa)Fe(OTf)2 (1) and (bpmen)Fe(OTf)(2) (2) [tpa = tris-(2-pyridylmethyl)amine; bpmen=N,N'-bis-(2-pyridylmethyl)-N,N'-dimethyl-1,2-ethylenediamine] were found to catalyze the in situ formation of AcOOH from H2O2 and AcOH in the course of olefin oxidations. While oxidation of cyclooctene by H2O2 catalyzed by 1 gives nearly equimolar epoxide and cis-diol products, introduction of AcOH to the reaction greatly enhances the selectivity for epoxidation. The resulting product distribution is nearly identical to that of cyclooctene oxidation by AcOOH catalyzed by 1. The in situ generation of AcOOH from H2O2 and AcOH in epoxidation catalyzed by some iron complexes opens a possibility to attain AcOOH-type efficiency of epoxidation using H2O2 as a terminal oxidant.
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