Anomalous behavior of the amides of benzo-and dibenzocrown thiocarboxylic acids under the conditions of methylation

During the reaction of the amides of benzo-and dibenzocrown thiocarboxylic acids with methyl iodide in the presence of potassium hydroxide they exhibit anomalous behavior leading to the nitriles of benzo-and dibenzocrown carboxylic acids. The nitriles of benzo-15-crown-5-, benzo-12-crown-4-, and dibenzo-18-crown-6-4′-carboxylic acids and the dinitriles of dibenzo-18-crown-6-and dibenzo-24-8-4′,4″(5″)-dicarboxylic acids were obtained. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 357–360, March, 2007.