Hydroxylation of Cycloalkanes Catalyzed by In(III)-, Tl(III)-Porphyrin

In(III)-, Tl(III)-porphyrin을 촉매제로 한 시클로알칸의 히드록시화 반응

The catalytic hydroxylation of several cycloalkanes in dichloromethane have been investigated using In(Ⅲ)-, Tl(Ⅲ)-porphyrin complexes as a catalyst and NaClO, $NaClO_{2}$, $H_{2}O_{2}$ as a terminal oxidant. Porphyrins were TPP and ($F_{20}$)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 $ C_{5} $ < $ C_{6}$ < $ C_{7}$ = $ C_{8}$. In this experimental condition $NaClO_2$ was rather efficient terminal oxidant than NaClO and $H_{2}O_{2}$.