Issue 0, 1971
From the journal:

Journal of the Chemical Society C: Organic

The Stobbe condensation. Part VIII. The cyclisation of trans-3-methoxycarbonyl-4-(2-thienyl)but-3-enoic acid and αβ-dithenylidene-succinic anhydride to the corresponding benzothiophen derivatives

(Mrs)S. M. Abdel-Wahhab  and  N. R. El-Rayyes  

Abstract

The condensation of thiophen-2-carbaldehyde with dimethyl succinate in the presence of potassium t-butoxide or sodium hydride gave predominantly trans-3-methoxycarbonyl-4-(2-thienyl)but-3-enoic acid, whose configuration is revealed by cyclisation with sodium acetate in acetic anhydride to the corresponding benzothiophen derivatives. Alcoholysis of the derived trans-3-caboxy-4-(2-thienyl)but-3-enoic anhydride yields the half-ester which is isomeric with the above mentioned half-ester. Condensation also gave the αβ-dithenylidenesuccinic acid in small amounts; its ratio depending upon the nature of the condensing agent. The derived anhydride yields on pyrolysis 4-(2-thienyl)benzothiophen-5,6-dicarboxylic anhydride.

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Article information

DOI
https://doi.org/10.1039/J39710003171
Article type
Paper

J. Chem. Soc. C, 1971, 3171-3173

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The Stobbe condensation. Part VIII. The cyclisation of trans-3-methoxycarbonyl-4-(2-thienyl)but-3-enoic acid and αβ-dithenylidene-succinic anhydride to the corresponding benzothiophen derivatives

S. M. Abdel-Wahhab and N. R. El-Rayyes, J. Chem. Soc. C, 1971, 3171 DOI: 10.1039/J39710003171

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