New Singlet Oxygen Source and Trapping Reagent for Peroxide Intermediates

I. Saito Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan

R. Nagata Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan

H. Nakagawa Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan

H. Moriyama Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan

T. Matsuura Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan

K. Inoue Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan; Department of Industrial Chemistry, Faculty of Engineering, Ehime University, Matsuyama, 790, Japan

Abstract

Application of newly-developed water-soluble singlet oxygen sources in the oxidation of biologically important compounds and the electron-transfer process involving singlet oxygen has been reviewed. Particularly, oxidation products of tryptophan by chemically generated singlet oxygen were compared to those obtained in dye-sensitizd photooxygenation. The usefulness of trimethylsilyl cyanide as a trapping reagent for dipolar peroxide intermediates has been demonstrated in the photooxygenation of N-methylindoles, 2-(methoxymethylene)adamantane and adamantylideneadamantane in aprotic solvents. Based on these trapping reactions mechanism of singlet oxygen reaction of electron-rich enol ethers and enamines is discussed in light of theoretical calculation.

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New Singlet Oxygen Source and Trapping Reagent for Peroxide Intermediates

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New Singlet Oxygen Source and Trapping Reagent for Peroxide Intermediates

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