Skip to Content
Merck
  • A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation.

A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation.

Molecules (Basel, Switzerland) (2015-05-15)
Baocheng Zhou, Wenxing Chen
ABSTRACT

Iron (III) phthalocyanine complexes were employed for the first time as a mild and efficient Lewis acid catalyst in the selective oxidation of cyclohexene to cyclohexane-1,2-diol. It was found that the catalyst FePcOTf shown excellent conversion and moderate selectivity relative to other iron (III) phthalocyanine complexes. The optimum conditions of the oxidation reaction catalyzed by FePcOTf/H2O2 have been researched in this paper. Iron (III) phthalocyanine triflate (1 mol %) as catalyst, hydrogen peroxide as oxidant, methanol as solvent, and a mole ratio of substrate and oxidant (H2O2) of 1:1 were used for achieving moderate yields of 1,2-diols under reflux conditions after eight hours.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Silver nitrate solution, 2.5 % (w/v) AgNO3 in H2O
Sigma-Aldrich
Silver trifluoromethanesulfonate, ≥99.95% trace metals basis
Sigma-Aldrich
Cyclohexene, inhibitor-free, ReagentPlus®, 99%
Sigma-Aldrich
Cyclohexene, contains 100 ppm BHT as inhibitor, ≥99.0%
Sigma-Aldrich
29H,31H-Phthalocyanine, β-form, 98%
Sigma-Aldrich
Silver trifluoromethanesulfonate, ≥99%
Sigma-Aldrich
Silver nitrate on silica gel, extent of labeling: ~10 wt. % loading, +230 mesh
Sigma-Aldrich
Cyclohexene oxide, 98%
Sigma-Aldrich
Silver nitrate, BioReagent, suitable for plant cell culture, >99% (titration)
Sigma-Aldrich
Silver nitrate, BioXtra, >99% (titration)
Sigma-Aldrich
2-Cyclohexen-1-ol, 95%
Sigma-Aldrich
2-Cyclohexen-1-one, ≥95%
Sigma-Aldrich
Silver nitrate, 99.9999% trace metals basis
Sigma-Aldrich
Silver nitrate, anhydrous, ≥99.999% trace metals basis