Fiesselmann thiophene synthesis

What is Fiesselmann thiophene synthesis?

The Fiesselmann thiophene synthesis involves the reaction of 1,3-dicarbonyl compounds or β-chlorovinyl aldehydes with thioglycolates or other thiols that contain a reactive methylene group. This intramolecular aldol condensation results in the formation of thiophene-2-carboxylic esters.

Fiesselmann thiophene synthesis - general reaction scheme
Fiesselmann thiophene synthesis

A modified version of this synthesis is often used to prepare various selenophenes.

References

H. Fiesselmann, “Verfahren zur Herstellung von Derivaten der 3-Oxythiophen-2-carbonsaeure” [Process for the preparation of derivatives of 3-oxythiophene-2-carboxylic acid] German Patent, 1957, DE 1020641

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