Alkyl substituted [2.2]paracyclophane-1,9-dienes

Benjamin J. Lidster, Dharam R. Kumar, Andrew M. Spring, Chin Yang Yu, Madeleine Helliwell, James Raftery, Michael L. Turner

    Research output: Contribution to journalArticlepeer-review

    27 Citations (Scopus)


    [2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

    Original languageEnglish
    Pages (from-to)6079-6087
    Number of pages9
    JournalOrganic and Biomolecular Chemistry
    Issue number25
    Publication statusPublished - 2016

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry


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