Hydroxyisooxophlorin is an oxidatively degraded porphyrin that contains one carbonyl carbon, one hydroxymethylene group, and two sp-methine groups at its meso positions. Here we report that oxidation of a free-base meso-hydroxyporphyrin with [bis(trifluoroacetoxy)iodo]benzene in the presence of HO afforded two regioisomers of hydroxyisooxophlorins, 10-hydroxy-10-iso-5-oxophlorin and 15-hydroxy-15-iso-5-oxophlorin, as major and minor products, respectively. We also examined the reaction mechanism, acid-mediated isomerization, metal complexation behavior, and physical properties of these molecules.
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Synthesis of Hydroxyisooxophlorins by Oxidative Degradation of meso-Hydroxyporphyrins.
Org Lett
June 2019
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering , Nagoya University, Nagoya 464-8603 , Japan.
Hydroxyisooxophlorin is an oxidatively degraded porphyrin that contains one carbonyl carbon, one hydroxymethylene group, and two sp-methine groups at its meso positions. Here we report that oxidation of a free-base meso-hydroxyporphyrin with [bis(trifluoroacetoxy)iodo]benzene in the presence of HO afforded two regioisomers of hydroxyisooxophlorins, 10-hydroxy-10-iso-5-oxophlorin and 15-hydroxy-15-iso-5-oxophlorin, as major and minor products, respectively. We also examined the reaction mechanism, acid-mediated isomerization, metal complexation behavior, and physical properties of these molecules.
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