Alkyl Substituted [2.2]Paracyclophane-­‐1,9-­‐dienes

Benjamin Lidster, Dharam Kumar, Andrew Spring, Chin Yu, Madeleine Helliwell, James Raftery, Michael Turner

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    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
    JournalOrganic and Biomolecular Chemistry
    Issue number25
    Early online date1 Jun 2016
    Publication statusPublished - 7 Jul 2016


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