CONVENIENT SYNTHESIS OF ALPHA-TERTHIENYL AND ALPHA-QUINQUETHIENYL VIA A FRIEDEL-CRAFTS ROUTE

MERZ, A and ELLINGER, F (1991) CONVENIENT SYNTHESIS OF ALPHA-TERTHIENYL AND ALPHA-QUINQUETHIENYL VIA A FRIEDEL-CRAFTS ROUTE. SYNTHESIS-STUTTGART (6). pp. 462-464. ISSN 0039-7881,

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Abstract

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 (alpha-terthienyl or alpha-quinquethienyl) in high yields. Attempted acylation of alpha-terthienyl leads to 5,5-bis[5-(2,2':5',2''-tertienyl)]tetrahydrofuran-2-one. As a side-product of the Friedel-Crafts acylation of thiophene a new indigo-like blue dye with alpha-quaterthienyl framework is isolated.

Item Type: Article
Uncontrolled Keywords: THIOPHENE OLIGOMERS;
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:46
URI: https://pred.uni-regensburg.de/id/eprint/54998

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