Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

L. Marin, S. Van Mierloo, Y. Zhang, K. Robeyns, B. Champagne, P. Adriaensens, L. Lutsen, D. Vanderzande, W. Maes

Research output: Contribution to journalArticle

Abstract

In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.
Original languageEnglish
Pages (from-to)2260-2267
Number of pages8
JournalTetrahedron
Volume69
Issue number10
DOIs
Publication statusPublished - 11 Mar 2013

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  • Projects

    PAI n°P7/05 - FS2: Functional Supramolecular Systems (FS2)

    CHAMPAGNE, B., De Vos, D., Van der Auweraer, M., Jérôme, C., Lazzaroni, R., Marin, G., Jonas, A., Du Prez, F., Vanderzande, D., Van Tendeloo, G., Van Speybroeck, V., NENON, S. & STAELENS, N.

    1/04/1230/09/17

    Project: Research

    Functional Supramolecular Systems (PAI P6/27)

    CHAMPAGNE, B., WOUTERS, J., BOTEK, E., DE WERGIFOSSE, M., GUTHMULLER, J., Liegeois, V., NORBERG, B., Plaquet, A., STAELENS, N. & Vercauteren, D.

    1/01/0731/12/11

    Project: Research

    Equipment

  • Datasets

    CCDC 912552: Experimental Crystal Structure Determination

    Adriaensens, P. (Contributor), CHAMPAGNE, B. (Contributor), Lutsen, L. (Contributor), Maes, W. (Contributor), Marin, L. (Contributor), Robeyns, K. (Contributor), Van Mierloo, S. (Contributor), Vanderzande, D. (Contributor) & Zhang, Y. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

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    Cite this

    Marin, L., Van Mierloo, S., Zhang, Y., Robeyns, K., Champagne, B., Adriaensens, P., Lutsen, L., Vanderzande, D., & Maes, W. (2013). Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones. Tetrahedron, 69(10), 2260-2267. https://doi.org/10.1016/j.tet.2013.01.026