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 journalArticlepeer-review

    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

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