Intramolecular Catalysis in Addition of Carboxyl to Carbon-Carbon Triple Bonds1

RL Letsinger, EN Oftedahl, JR Nazy

文献索引：Letsinger,R.L. et al. Journal of the American Chemical Society, 1965 , vol. 87, # 4 p. 742 - 749

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被引用次数: 27

摘要

Aspects of the mechanism of addition of a carboxylic acid to a carbon-carbon triple bond were investigated with tolan compounds bearing carboxyl substituents. It was found that 2, 2'- tolandicarboxylic acid (I) isomerizes readily in alcohol solution at room temperature to 3-(2- carboxybenzylidene) phthalide (IV), which in turn rearranges to 3-(2-~ arboxyphenyI) isocoumarin (VI) and a dilactone when warmed in an acetic-sulfuric acid solution. 2- ...