1996 Fiscal Year Final Research Report Summary
Exploitation of Electrochemical Reaction System suitable for Oxidation of Hardly Oxidizable Organic Compounds
| Project/Area Number |
06555273
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 試験 |
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| Research Field |
有機工業化学
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| Research Institution | Nagasaki University |
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Principal Investigator |
MATSUMURA Yoshihiro Nagasaki University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (60026309)
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| Co-Investigator(Kenkyū-buntansha) |
WATANABE Mitsuaki Nagasaki University, Center for Instrumental Analysis, Associate Prof., 計測分析センタ, 助教授 (10039654)
KINOSHITA Toshio Nagasaki University, Pharmaceutical Sciences, Associate Prof., 薬学部, 助教授 (60039641)
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| Project Period (FY) |
1994 – 1996
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| Keywords | Electrochemical Oxidation / Trifluoroethanol / Solvent Effect / Trifluoroethylamine / Mediator |
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| Research Abstract |
Electrochemical oxidation has a variety of advantages in comparison with conventional oxidation methods. For example, the oxidation of organic compound is achieved without any use of oxidizing reagents. However, the oxidation of organic compounds possessing high oxidation potentials has been so far difficult by electrochemical method. The purpose of this study was to exploit solvent systems suitable for efficient oxidation of such organic compounds. The following results were obtained.
i) Electorhchemical oxidation in trifluoroethanol : N-Methoxycarbonyl-2,2,2-trifluoroethylamine, hardly oxidizable compound, could be oxidized by electrochemical oxidation in trifluoroethanol solvent system.
ii) Electorchemical oxidation of aromatic compounds substituted with electron-withdrawing group : Electrochemical oxidation of toluene derivatives possessing electron-withdrawing group in trifluoroethanol solvent system gave the acetals of the corresponding benzaldehyde derivatives.
iii) Electorchemical oxidation of ethers : Aliphatic saturated ethers were oxidized in trifluoroethanol solvent system to give alpha-trifluoroethoxylated ethers.
iv) Electrochemical oxidation of gamma-butyrolactones : Trifluoroethanol solvent system allowed us to oxidize gamma-butyrolactones, which has not been oxidized by conventional oxidation methods.
v) Exploitation of highly efficient reaction systems : Reaction conditions for large scale electrochemical oxidation of organic compounds as described above were scrutinized (electrode materials, temperature, current density, and so on). The use of thioanisole as a mediator gave a good result in respect of current efficiencies.
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