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Synthesis 1991; 1991(6): 462-464
DOI: 10.1055/s-1991-26494
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Convenient Synthesis of α-Terthienyl and α-Quinquethienyl via a Friedel-Crafts Route

Andreas Merz* , Franz Ellinger
  • *Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, D-8400 Regensburg, Germany
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Publication Date:
29 April 2002 (online)

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Thiophene and bithiophene are converted into 1,4-bis(2-thienyl)-1,4-butanedione and the corresponding bis(bithienyl) substituted diketone, respectively, by acylation with succinyl chloride/aluminum chloride in dichloromethane or 1,2-dichloroethane. Reaction of the diketones with Lawesson's reagent gives 2,2′: 5′,2″-terthiophene or 2,2′:5′,2″:5″,2′′′:5′′′,2′′′′-quinquethiophene (α -terthienyl or α-quinquethienyl) in high yields. Attempted acylation of α-terthienyl leads to 5,5-bis[5-(2,2′:5′,2″-terthienyl)] tetrahydrofuran-2-one. As a side-product of the Friedel-Crafts acylation of thiophene a new indigo-like blue dye with α-quaterthienyl framework is isolated.