Continuous In Situ Electrogeneration of o-Benzoquinone in Microreactor: Application to High Yield Reaction with Benzenethiols

被引：26
作者：
Kashiwagi, Tsuneo [1 ]
Amemiya, Fumihiro [1 ]
Fuchigami, Toshio [1 ]
Atobe, Mahito [1 ,2 ]
机构：
[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan
[2] Yokohama Natl Univ, Dept Environm & Syst Sci, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
来源：
JOURNAL OF FLOW CHEMISTRY | 2013年 / 3卷 / 01期
关键词：
electrosynthesis; o-quinone; Michael addition; unstable compound; diphenylsulfide synthesis; FACILE ELECTROCHEMICAL METHOD; PARALLEL LAMINAR-FLOW; SILYL ENOL ETHERS; ELECTROORGANIC SYNTHESIS; ORTHO-QUINONES; OXIDATION; CHEMISTRY; CATECHOLS;
D O I：
10.1556/JFC-D-12-00019
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have successfully demonstrated that a microflow reactor is extremely useful in controlling reactions involving an unstable o-benzoquinone. As a model reaction, Michael addition reaction between o-benzoquinone generated from electrochemical oxidation of catechol and benzenethiols was employed. This reaction system enables selective oxidation of catechol avoiding the oxidation of benzenethiol, although these oxidation potentials are close to each other. The examination of several reaction conditions indicated that the key features of the method are an effective o-benzoquinone generation and its rapid use for the following reaction without decomposition in a microflow system. In addition, cyclic voltammetry measurements elucidated that catechol concentration and selection of anode material were crucial factors for effective o-quinone generation.
引用
收藏
页码：17 / 22
页数：6
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