Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction

Al-jumaili, Mustafa A-jabbar and Woodward, Simon (2017) Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction. Tetrahedron, 73 (40). pp. 5847-5852. ISSN 0040-4020

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Abstract

Derivatives of 3,4-ethylenedithiothiophene (EDTT) are reported starting from tetrabromothiophene. Selective 2,5-dilithiation followed by reaction with a range of aldehydes gives diols as mixtures of diastereomers. Only the 2 and 5 positions in thiophene react leaving the 3,4-bromides for further elaboration. The diols are oxidised to their corresponding diketones using activated MnO2. Reaction with 1,2-ethanedithiol, by addition-elimination, provides access to novel monomers for the preparation of conjugated copolymers of 3,4-ethylenedithiothiophene (EDTT). A range of these monomers can be attained by applying the synthesis of a series of ketones applicable to further synthesis of π-extended thiophene-based organic semiconductors. Finally, this new route was compared to 3,4-ethylenedioxythiophene (EDOT) dialdehyde derivatives synthesised by an alternative to literature chemistry.

Item Type: Article
Keywords: Addition-elimination reaction; 3,4-Ethylenedithiothiophene; 1,2-Ethanedithiol; Organic semiconductors; EDTT
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1016/j.tet.2017.08.026
Depositing User: Smith, Ruth
Date Deposited: 08 Sep 2017 10:05
Last Modified: 13 Oct 2017 04:59
URI: http://eprints.nottingham.ac.uk/id/eprint/45539

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