Abstract
Abstract Current efficiency for the (Br)+(positive bromine species)-mediated indirect electrooxidation of alcohols to the corresponding carbonyl compounds decreased with increase in Br− concentration in dichloromethane and aqueous acidic solutions, while no concentration dependence was observed in an aqueous neutral solution. These facts suggested a general and practical guideline for the indirect electrooxidation, i.e. low Br− concentration is favorable in an electrolytic solution of low nucleophilicity. It was also found that the kind of (Br)+ species formed anodically in the absence of the alcohols in dichloromethane clearly depended on charge(Q) passed as follows: Br3− at Q≤2⁄3F mol−1 (1F=96480 C), Brn− (n>3) at 2⁄3<Q<1F mol−1, and Br2 at Q=1F mol−1. Among these species, Br3− and Br2 seemed to be the weakest and strongest oxidizing agents, respectively. Lower efficiency for the indirect electrooxidation in higher Br− concentration was rationalized as due to more predominant formation of Br3− and/or Brn− with smaller n values.
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