Catalyzed Oxidation of Cyclohexene and Cyclooctene with First Row Transition Metallophthalocyanines

摘要

First row transition metal complexes of phthalocyanine are employed as catalysts for the oxidation of cyclohexene and cyclooctene using iodosylbenzene and pentafluoroiodosyl benzene. The catalysis was performed in dichloromethane:methanol:water (80:18:2) solvent mixture. The products of the catalysis for cyclohexene are epoxycyclohexane, 2-cyclohexene-1-ol and 2-cyclohexene-1-one whereas for cyclooctene it is specifically cyclooctene oxide. For cyclohexene oxidation epoxide yield and selectivity is in the order of Mn~Ⅱ > Fe~Ⅲ > Fe~Ⅱ > Co~Ⅱ > Cr~Ⅲ > Ni~Ⅱ > Cu~Ⅱ, while for 2-cyclohexene-1-one production the ability of the catalysts are in the order of Ni~Ⅱ > Co~Ⅱ > Cu~Ⅱ > Cr~Ⅲ > Fe~Ⅲ > Fe~Ⅱ > Mn~Ⅱ.