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KMID : 1059519950390050364
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Journal of the Korean Chemical Society
1995 Volume.39 No. 5 p.364 ~ p.370
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Catalytic Activity of Ga(Ⅲ)-, In(Ⅲ)- and Tl(Ⅲ)-porphyrin Complexes
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Park Yu-Chul
Na Hun-Gil
Kim Seong-Su
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Abstract
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The catalytic oxidations of several olefins in CH2Cl2 have been investigated using non-redox metalloporphyrin (M=Ga(Ⅲ), In(Ⅲ), Tl(Ⅲ)) complexes as catalyst and sodium hypochlorite as terminal oxidant. Porphyrins were (p-CH3O)TPP, (p-CH3)TPP, TPP, (p-F)TPP, (p-Cl)TPP and (F20)TPP (TPP=tetraphenylporphyrin), and olefins were (p-CH3O)-, (p-CH3)-, (p-H)-, (p-F)-, (p-Cl)- and (p-Br)styrene and cyclopentene and cyclohexene. The substrate conversion yield was discussed according to the substituent effects of metalloporphyrin and substrate, and the radius effect of non-redox metal ion. 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. But the substituent effect of substrate on the conversion yield decreased with increasing the σ+ values on substrates in the order of p-CH3O > p-CH3 > H > p-Cl > p-Br. For the oxidation of several olefins, the complexes of In(Ⅲ)- and Tl(Ⅲ)-porphyrins turned out to be more active catalysts than Ga(Ⅲ)-porphyrin.
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