SYNTHESIS OF α-THIOPHENE OLIGOMERS VIA ORGANOTIN COMPOUNDS

A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Thus, substituted α-bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 2-trimethylstannylthiophene. The latter reagent coup...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1997-07, Vol.126 (1), p.65-74
Main Authors: Kamal, Marwan R., Al-taweel, Samir A., El-abadelah, Mustafa M., Abu Ajaj, Khalid M.
Format: Article
Language:English
Subjects:
2-stannylthiophenes
Functionalized α-thiophene oligomers
synthesis
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Summary:A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Thus, substituted α-bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 2-trimethylstannylthiophene. The latter reagent couples with 2,5-dibromothiophenes to give the α-terthiophenes which are also accessible through the reaction of 5-trimethylstannyl-α-bithiophene with 2-bromothiophenes. 2,5-Bis(trimethylstannyl) thiophene and 5,5′-bis(trimethylstannyl)-α-bithiophene react with 2-bromothiophenes to give α-terthiophenes and α-quaterthiophenes, respectively. α-Quaterthiophene is also produced via the reaction of 5-trimethylstannylthiophene with 5,5′- dibromo-α-bithiophene. The coupling reaction of 5-tnmethylstannyl-α-bithiophene with 2.5-dibromothiophene affords the α-quinquethiophene. The structures of the new compounds were confirmed by elemental analysis, Mass spectrometry, 1 H- and 13 CNMR spectral data.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509708043546