PECULIARITIES OF THE BEHAVIOR OF SUCCINYL DICHLORIDE IN FRIEDEL-CRAFTS REACTION WITH THIOPHENES

Authors

  • В. И. Смирнов M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 119571
  • А. В. Афанасьев M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 119571
  • Л. И. Беленький N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991

DOI:

https://doi.org/10.1007/5247

Keywords:

4, 4-di(2-thienyl)but-3-enoic acids, 4-di(2-thienyl)butyrolactones, 4-oxo-4-(2-thienyl)butyric acids, succinyl dichloride, 1, 4-(2-thienyl)butane-1, 4-diones, thiophenes, acylation.

Abstract

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.

How to Cite
Smirnov, V. I.; Afanas'ev, A. V.; Belen'kii, L. I. Chem. Heterocycl. Compd. 2011, 46, 1199. [Khim. Geterotsikl. Soedin. 2010, 1485.]

For this article in the English edition see DOI 10.1007/s10593-011-0653-z

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Published

2019-07-08

Issue

No. 10 (2010)

Section

Original Papers