Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction
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 ela...
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Elsevier
2017
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| Online Access: | https://eprints.nottingham.ac.uk/45539/ |
| _version_ | 1848797150327078912 |
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| author | Al-jumaili, Mustafa A-jabbar Woodward, Simon |
| author_facet | Al-jumaili, Mustafa A-jabbar Woodward, Simon |
| author_sort | Al-jumaili, Mustafa A-jabbar |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:59:18Z |
| format | Article |
| id | nottingham-45539 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:59:18Z |
| publishDate | 2017 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-455392020-05-04T19:10:37Z https://eprints.nottingham.ac.uk/45539/ Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction Al-jumaili, Mustafa A-jabbar Woodward, Simon 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. Elsevier 2017-10-05 Article PeerReviewed 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 Addition-elimination reaction; 3 4-Ethylenedithiothiophene; 1 2-Ethanedithiol; Organic semiconductors; EDTT http://www.sciencedirect.com/science/article/pii/S0040402017308578?via%3Dihub doi:10.1016/j.tet.2017.08.026 doi:10.1016/j.tet.2017.08.026 |
| spellingShingle | Addition-elimination reaction; 3 4-Ethylenedithiothiophene; 1 2-Ethanedithiol; Organic semiconductors; EDTT Al-jumaili, Mustafa A-jabbar Woodward, Simon Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title | Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title_full | Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title_fullStr | Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title_full_unstemmed | Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title_short | Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction |
| title_sort | efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (edtt) via addition-elimination reaction |
| topic | Addition-elimination reaction; 3 4-Ethylenedithiothiophene; 1 2-Ethanedithiol; Organic semiconductors; EDTT |
| url | https://eprints.nottingham.ac.uk/45539/ https://eprints.nottingham.ac.uk/45539/ https://eprints.nottingham.ac.uk/45539/ |