The catalytic oxidation reaction of several cycloolefins in CH2Cl2 have been investigated using non-redox metalloporphyrin(M = Ga(III), In(III) and TI(III) complexes as a catalyst and sodium hypochlorite as a terminal oxidant. Porphyrins were (p-CH3O)TPP, (p-CH3)TPP, TPP, (p-F)TPP, (p-Cl)TPP and (F20)TPP (TPP=5,10,15,20-tetraphenyl-21H,23H-porphyrin) and olefins were cyclopentene, cyclohexene, cycloheptene and cyclooctene, The substrate conversion yield(%) was investigated according to the radius effect of non-redox metal ion, substituent effect and hindrance effect of metalloporphyrin. The conversion yield of cycloolefin was in the following order : C5 〈 C6 〈 C7 = C8.

The catalytic activities of several metalloporphyrin, wherein the porphyrins are TPP(5,lO,l5,20-Tetraphenyl-21H,23H-porphyrin) and (p-X)TPP (X =CH3O, CH3, F, Cl), are reported for the oxidation of styrene and it's derivatives. The electronic effects of substrates and porphyrins on the catalytic activity of metalloporphyrin containing the transition metal ion such as Mn(III) was discussed. Investigating the correlation between the Michaelis-Menten's rate parameters and the substituent constants, we are going to analyze the influences on the changes of catalytic activity or rate determining step during the processes of the formation and the dissociation of the M-oxo-olefin.

The catalytic hydroxylation of several cycloalkanes in dichloromethane have been investigated using In(Ⅲ)-, Tl(Ⅲ)-porphyrin complexes as a catalyst and NaClO, NaClO2, H2O2 as a terminal oxidant. Porphyrins were TPP and (F20)TPP (TPP = tetraphenylporphyrin) and substrates were cyclopentane, cyclohexane, cycloheptane and cyclooctane. The substrate conversion yield was discussed according to the substituent effect and hinderance effect of metalloporphyrin and the radius effect of non-redox metal ion. The conversion yield of cycloalkane followed the order of C5 〈 C6 〈 C7 = C8. In this experimental condition NaClO2 was rather efficient terminal oxidant than NaClO and H2O2.

The catalytic oxidations of several cycloolefins in CH2Cl2 were been investigated using Mn(III)-, Fe(III)-porphyrin complexes as a catalyst and sodium hypochlorite as a terminal oxidant. Porphyrins were (p-CH3O)TTP, (p-CH3)TTP, TPP, (p-F)TPP, (p-Cl)TPP and (F20)TPP (TPP = tetraphenylporphyrin), and olefins were cyclopentene, cyclohexene and cycloheptene. The substrate conversion yield was discussed according to the substituent effects of metalloporphyrin. The conversion yield of substrate by changing the substituent of TPP increased in the order of p-CH3O 〈 p-CH3 〈 H 〈 p-F 〈 p-Cl, which was consistent with the sequence of 4Σ values of TPP. The conversion of cycloalkene followed the order of C5 < C6 < C7.