N-ヒドロキシ-2-チオピリドンを用いた有機ラジカル反応の展開

抄録

Various kinds of carboxylic acids have been converted to the corresponding sulfides, halides, hydrocarbons, selenides and tellurides, peroxides, and alcohols directly via the radical decarboxylative reactions of the acyl esters (activated esters) of N-hydroxy-2-thiopyridone under the irradiation (tungsten lump) or heating (mainly in benzene) conditions, and further the addition products of the formed decarboxylated alkyl radical to the active olefinic compounds (phenyl vinyl sulfone, nitroethylene, ethyl acrylate etc) have been obtained in good yields. These addition products were further converted to the C₁ homologated sulfides, C₁ homologated carboxylic acids, aldehydes, ketones, and phosphorus compounds. Finally, the same kinds of radical decarboxylative reactions were applied to, form the corresponding alkoxycarbonyl, alkoxy, and amino radicals starting from alcohols and amines, respectively. Therefore the radical reactions with N-hydroxy-2-thiopyridone are very rich chemistry.