Reduction of some sulfides and ethers with aromatic rings by electrochemically generated solvated electrons.
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概要
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The reduction of some sulfides and ethers has been investigated in 0.5 M LiCl–HMPA solutions with and without alcohol (methanol, ethanol, and 2-propanol). Diphenyl sulfide underwent cleavage to produce benzene as the main product. The hydrogenated products of benzene have been obtained in 35 and 50 mol % alcohol solutions, and the increased dependence on ethanol (<I>i.e.</I>, H<SUP>+</SUP>) concentrations in the solutions has been established. The cleavage reaction was affected by the ease of α-hydrogen abstraction from the alcohol. The cleavage reaction has been elucidated as proceeding <I>via</I> a one-electron transfer mechanism, while the hydrogenation proceeded <I>via</I> a two-electron transfer mechanism. The estimation of current efficiencies supports this mechanism. Hexyl phenyl sulfide cleaved in the manner similar to that for diphenyl sulfide with a current efficiency of about 80% whereas only the hydrogenated products were obtained from benzo[<I>b</I>]thiophene and dibenzothiophene. Fission of the C–S bond of tetrahydrothiophene has been achieved by this method. Some ethers examined exhibited <I>approx.</I> the same behavior as the corresponding sulfides.
- 公益社団法人 日本化学会の論文
著者
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Miyake Mikio
Department Of Surgery Tamano Mitsui Hospital
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NAKAYAMA Yoshihiro
Department of Cardiovascular Surgery, Kumamoto Central Hospital
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Nomura Masakatsu
Department Of Applied Chemistry Faculty Of Engineering Osaka University
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Kikkawa Shoichi
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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