New singlet oxygen source and trapping reagent for peroxide intermediates.
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-sensitized 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.
D003486:Cyanides; D004583:Electrons; D005609:Free Radicals; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010100:Oxygen; D010545:Peroxides; D010777:Photochemistry; D012995:Solubility; D012997:Solvents; D014297:Trimethylsilyl Compounds; D014364:Tryptophan
D003486:Cyanides; D005609:Free Radicals; D010545:Peroxides; D012997:Solvents; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide; D014364:Tryptophan; D010100:Oxygen