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Visible Light Induced Oxygenation of Cyclohexene With Activation of Water Sensitized By Dihydroxy Coordinated Tetraphenylporphyrinatotin(Iv)

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image of Research on Chemical Intermediates

Visible light irradiation of a reaction mixture containing dihydroxy coordinated tetraphenylporphyrinatotin(IV), cyclohexene and potassium hexachloroplatinate induced oxygenation of the cyclohexene under degassed conditions. In the reaction system, a water molecule served as the oxygen donor. Cyclohex-2-enol, 1,2-dichlorocyclohexane and 2-chlorocyclohexanol were the major oxidation products and the quantum yield was around 0.1. An experiment using H218O revealed that an 18O atom was quantitatively incorporated into the oxygenated products. The reaction was initially induced by an electron transfer from an excited triplet porphyrin to potassium hexachloroplatinate producing a cation radical of the porphyrin. Metal-oxo type complexes formed through deprotonation of the hydroxy group of the porphyrin cation radical were key reactive intermediates reacting with cyclohexene. Two kinds of the metal-oxo type complex reactive intermediate were kinetically demonstrated to be involved in the reaction system, producing different oxidation products from cyclohexene.

Affiliations: 1: Department of Applied Chemistry, Graduate Course of Engineering, Tokyo Metropolitan University, 1-1 Minami-ohsawa, Hachiohji, Tokyo 192-0397, JAPAN


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