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Synthesis 1989; 1989(3): 210-211
DOI: 10.1055/s-1989-27202
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Eine einfache Synthese 3,5- und 2,3,5-alkyl- und -arylsubstituierter Thiophene

Karl Eichinger* , Peter Mayr, Peter Nussbaumer
  • *Institut für Organische Chemie der Technischen Universität Wien, Abteilung für Chromatographie und Spektroskopie, Getreidemarkt 9, A-1060 Wien, Austria
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Publikationsdatum:
17. September 2002 (online)

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A Simple Synthesis of 3,5- and 2,3,5-Alkyl- or -Aryl-Substituted Thiophenes α-Bromo- and α-chloroalkanones react readily with tert-butylmercaptan according to Lissel1 to give 2-(tert-butylthio)ketones. Reaction of these ketones with the 1-alkynylmagnesium halides derived from phenylacetylene or 1-hexyne affords unstable mixtures of stereoisomeric 2-(tert-butylthio)-1-(1-alkynyl)alkanols which, upon treatment with hot aqueous acid, give 3,5-di- or 2,3,5-trisubstituted thiophenes in overall yields from 36 to 90%.