Abstract

The active species formed by the electron transfer between substrate and electrode show a variety of unique reactivities and selectivities since electron transfer takes place in the special environment created in the boundary layer between electrode and solution. Interestingly, the anion radical generated by the transfer of one electron to a carbonyl group coupled with an aromatic ring. The electroreductive intramolecular coupling reaction of a carbonyl group was also achievable with cycloheptatriene systems. The electrochemical reduction of a mixture of a simple olefin and a ketone at a solid graphite cathode in a mixed solvent of dioxane and 2-propanol did not give coupled product in a satisfactory yield. The cathodic reduction of Ketones in the presence of O-methyl oximes gave intermolecular coupling products, 2-methoxyamino alcohols, which were easily reducible to 2-amino alcohols.

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