Carboxylation of Nitromethane by Carbon Dioxide and Potassium Phenoxide Derivatives. Substituent Effect upon the Yield of Carboxylate

概要

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The carboxylation of nitromethane with carbon dioxide proceeded in the presence of potassium phenoxides in DMF, yielding dipotassium nitroacetate as a precipitate. This reaction proceeded well at 0℃. The substituent effect upon the carboxylation was investigated by using potassium phenoxides with various substituents (p-OCH_3,p-CH_3,H, p-Cl, m-Cl, p-COCH_3,and p-NO_2). The reaction was completed in 5 min at 0℃. The maximum yield of carboxylate was obtained when unsubstituted phenoxide was used ; the yield of carboxylate was low when potassium phenoxide with a substituent having a highly negative or highly positive σ value was used. The mechanism of the carboxylation is discussed. The formation of the carboxylate as a precipitate is considered to be an important factor. Methods for the effective transformation of dipotassium nitroacetate to methyl nitroacetate are briefly surveyed.
公益社団法人日本薬学会の論文
1984-06-25