Electrochemical Haloform Reaction Efficient Transformation of Methyl Ketones to Carboxylates.

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  • 電気化学的ハロホルム反応メチルケトン類からエステル類への効率的変換
  • Electrochemical Haloform Reaction Effic

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Abstract

Electrolysis of aliphatic, aromatic, and α, β-unsaturated methyl ketones in an anhydrous alcohol containing sodium or lithium bromide using an undivided cell equipped with carbon rods as the anode and the cathode brought about electrochemical Haloform reaction to give the corresponding carboxylates in good to excellent yields. The reaction was found to be mediated with bromonium ion, generated by anodic oxidation of bromide ion. Absence of bromoform in the product mixtures of this reaction may be attributed to ready reduction of bromoform to highly volatile compounds, which may provide high simplicity of reaction procedure.<BR>Facile and efficient introduction of carboalkoxyl groups to aromatic rings and olefinic bonds was accomplished in two steps through initial Friedel-Crafts acetylation followed by the present electrochemical method.

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