Synthesis and ring-opening metathesis of tetraalkoxy-substituted [2.2]paracyclophane-1,9-dienes

Chin Yang Yu, Madeleine Helliwell, James Raftery, Michael L. Turner

    Research output: Contribution to journalArticlepeer-review


    Tetraalkoxy-substituted [2.2]paracyclophane-1,9-dienes can be prepared in three steps from dithia- ACHTUNGTRENUNG[3.3]paracyclophanes. A mixture of pseudo-geminal and pseudo-ortho diastereomers is produced and the pure compounds can be separated by fractional crystallization. The solid state structures of these diastereomers reveal strongly distorted aromatic rings consistent with high levels of ring strain. Reaction of these diastereomers with the second generation Grubbs catalyst shows that only the pseudo-geminal isomer can be ring opened to give cis,trans-distrylbenzenes. The origin of this selectivity is discussed and the photoisomerization of the as-formed cis,- trans-product to the all trans isomer is demonstrated. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Original languageEnglish
    Pages (from-to)6991-6997
    Number of pages6
    JournalChemistry - A European Journal
    Issue number25
    Publication statusPublished - 14 Jun 2011


    • cyclophanedienes
    • isomers
    • metathesis
    • phenylenevinylenes
    • strained molecules


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