Exploitation of Electrochemical Reaction System suitable for Oxidation of Hardly Oxidizable Organic Compounds

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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.