Convenient Synthesis of α-Terthienyl and α-Quinquethienyl via a Friedel-Crafts Route

Andreas Merz; Franz Ellinger

doi:10.1055/s-1991-26494

Synthesis 1991; 1991(6): 462-464
DOI: 10.1055/s-1991-26494

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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.

PDF (252 kb)