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- W2050426023 abstract "The photochemistry of thianthrene (1) in the presence of a variety of electron acceptors in acetonitrile/water has been investigated. Diffusion-limited rates of fluorescence quenching were observed on excitation of 1 (with fumaronitrile and with methyl phthalate). Alternatively, addition of 1 led to quenching of the fluorescence emission of ketones, biacetyl, and fluorenone and to the quenching of the excited triplet states of quinones such as 2,5-dichloro-p-benzoquinone (5) and 9,10-anthraquinone (3). Steady irradiation of 1 with selected acceptors results in photooxidation yielding the sulfoxide (2) and the expected photoreduction products. The electron-transfer mechanisms were further studied by laser flash photolysis. The quenching of ketone triplets by 1 resulted in formation of the radical cation of 1([lambda][sub max]540 nm). The decay of this species and its dependence on the concentration of water present were determined; the bimolecular rate constant for trapping of 1[sup [center dot]+] by water in acetonitrile-water solution is 4.9 x 10[sup 4] M[sup [minus]1]s[sup [minus]1] under conditions in which 5 acts as a sensitizer. The nucleophilic trapping of the 1 radical cation by imidazole ([kappa] = 3.6 x 10[sup 7] M[sup [minus]1] s[sup [minus]1]) was also investigated. The mechanism of photoinduced two-electron oxidation of 1 and the role playedmore » by nucleophiles in facilitating the reaction are discussed in detail. 37 refs., 9 figs., 2 tabs.« less" @default.
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- W2050426023 date "1993-04-01" @default.
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- W2050426023 title "Electron-transfer photochemistry of thianthrene. Nucleophile-assisted photooxidation to sulfoxide" @default.
- W2050426023 doi "https://doi.org/10.1021/jo00060a016" @default.
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