Photocatalytic oxygenation of 10-methyl-9,10-dihydroacridine by O₂ with manganese porphyrins.

ABSTRACT: Photocatalytic oxygenation of 10-methyl-9,10-dihydroacridine (AcrH2) by dioxygen (O2) with a manganese porphyrin [(P)Mn(III): 5,10,15,20-tetrakis-(2,4,6-trimethylphenyl)porphinatomanganese(III) hydroxide [(TMP)Mn(III)(OH)] (1) or 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinatomanganese(III) acetate [(TPFPP)Mn(III)(CH3COO)] (2)] occurred to yield 10-methyl-(9,10H)-acridone (Acr═O) in an oxygen-saturated benzonitrile (PhCN) solution under visible light irradiation. The photocatalytic reactivity of (P)Mn(III) in the presence of O2 is in proportion to concentrations of AcrH2 or O2 with the maximum turnover numbers of 17 and 6 for 1 and 2, respectively. The quantum yield with 1 was determined to be 0.14%. Deuterium kinetic isotope effects (KIEs) were observed with KIE = 22 for 1 and KIE = 6

SUBMITTER: Jung J 

PROVIDER: S-EPMC4136676 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature