Preparation of 2-Thienyl Carboxylic Acids via 1,2-Thienyl Migration

Abstract

Abstract: 2-(2-Thienyl)propionic acid, 2-(5-bromo-2-thienyl) propionic acid and 2-(5-ethyl-2-thienyl)propionic acid were prepared from α-haloa]kyl thienyl ketones. The effects of the shift groups, alkyl substituents, leaving groups of the ketones, catalysts, temperature and solvents etc. on the rearrangement were studied. An optical active 2-(5-ethyl-2-thienyl)propionic acid was obtained in a high yield. It may be concluded that the 1,2-thienyl migration belongs to the electronic-lacking rearrangement with S_N2 mechanism.

Key words: 1,2-migration rearrangement, Thienyl carboxylic acids, Asymmetric synthesis

TrendMD:

Wang Jian-hua, Zhang Xi-guo . Preparation of 2-Thienyl Carboxylic Acids via 1,2-Thienyl Migration[J]. Chem. J. Chinese Universities, 1991, 12(7): 897.

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Preparation of 2-Thienyl Carboxylic Acids via 1,2-Thienyl Migration

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