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Electron transfer in the peroxytrifluoroacetic acid-assisted sulfoxidation and oxidative destruction of benzhydryl sulfides |
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| Authors: | A. R. Akopova A. S. Morkovnik V. N. Khrustalev A. V. Bicherov |
| Affiliation: | 1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp, Stachki, 344090, Rostov-on-Don, Russian Federation 2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation 3. Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov-on-Don, Russian Federation |
| Abstract: | The reactions of benzhydryl sulfides Ph2CHSCH2R (R = H, CONH2, COOH, CN) with peroxytrifluoroacetic acid in CF3COOH were studied experimentally and by the quantum chemical density functional theory (DFT) method and exhibited an unusual dependence on the substituent R. When R≠H, a complicated oxidative destruction of the substrates occurs to form 2,4,6-tribenzhydrylphenol as one of the products, while in the case of R = H, the starting benzhydryl sulfide is smoothly sulfoxidated. This fact is due to the common electron transfer from the substrate to reagent at the initial step and the difference in subsequent transformations of the species formed. |
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