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Peculiarities of the behavior of succinyl dichloride in Friedel-Crafts reaction with thiophenes*

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of thiophene, 2-methyl-, and 2-bromothiophene with succinyl dichloride in the presence of AlCl3, TiCl4, and SnCl4 have been studied. The effect of the acylation conditions, the relative amounts and nature of the Lewis acid on the ratio and yields of the 1,4-di(2-thienyl)-1,4-diones and 4-oxo-4-(2-thienyl)butyric acids formed have been demonstrated. Under the reaction conditions, the formation of 4,4-di(2-thienyl)but-3-enoic acids (the main products in many cases) and also 4,4-di(2-thienyl)-butyrolactones was demonstrated.

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Correspondence to L. I. Belen’kii.

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*Dedicated to the memory of an outstanding heterocyclic chemist and unsurpassed editor, Alexey Nikolaevich Kost,

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1485-1496, October, 2010.

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Smirnov, V.I., Afanas’ev, A.V. & Belen’kii, L.I. Peculiarities of the behavior of succinyl dichloride in Friedel-Crafts reaction with thiophenes*. Chem Heterocycl Comp 46, 1199–1207 (2011).

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