Abstract
The methyl esters of β-(2,5-di-tert-butyl-3-thenoyl)propionic and γ-(2,5-di-tert-butyl-3-thenoyl)butyric acids are deacylated by prolonged refluxing with a mixture of hydrochloric and formic acids to form di-tert-butylthiophene and aliphatic dicarboxylic acids (succinic and glutaric acids, respectively). The same process also occurs on heating 2,5-di-tert-butyl-3-acetylthiophene under the same conditions. Practically no deacylation occurs on refluxing these thiophene derivatives with hydrochloric acid alone or with a mixture of hydrochloric acid and acetic acid. Attempts to deacylate methyl β-(2,5-diethyl-3-thenoyl)propionate were unsuccessful. Assumptions regarding the peculiarities of deacylation in the 2,5-dialkyl-3-acylthiophene series associated with the geometry of the thiophene ring are expressed.
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