Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

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

    Research output: Contribution to journalArticle

    Abstract

    In this Letter we report on the reaction of 4H-cyclopenta[2,1-b:3,4- b′]dithiophen-4-one with various trivalent organophosphorus derivatives, with an emphasis on the final products depending on the applied reagents. No reaction occurred upon treatment with either triphenyl- or tricyclohexylphosphine, whereas addition of triethyl phosphite or tri(n-butyl)phosphine resulted in pinacol rearrangement. Structure elucidation of the isolated 5H-spiro(benzo[1,2-b:6,5-b′]dithiophene-4,4′- cyclopenta[2,1-b:3,4-b′]dithiophen)-5-one was achieved by combined NMR experiments, theoretical chemical shift and geometry calculations, and single crystal X-ray analysis.
    Original languageEnglish
    Pages (from-to)526-529
    Number of pages4
    JournalTetrahedron Letters
    Volume54
    Issue number6
    DOIs
    Publication statusPublished - 6 Feb 2013

    Fingerprint Dive into the research topics of 'Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one'. Together they form a unique fingerprint.

  • 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 906131: Experimental Crystal Structure Determination

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

    Dataset

    Cite this