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  • The stereoselectivity of addition of benzoyloxyl radicals to trans-A2-octalin

    Author(s)
    Busfield, WK
    Byriel, KA
    Grice, ID
    Jenkins, ID
    Lynch, DE
    Griffith University Author(s)
    Jenkins, Ian D.
    Grice, Darren D.
    Year published
    2000
    Metadata
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    Abstract
    The stereochemistry of addition of benzoyloxyl radicals to the conformationally rigid cyclohexene, trans-2-octalin, in the presence of the free radical scavenger 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxyl, is reported. Axial addition was favoured over equatorial addition with modest selectivity (axialequatorial = 1.71.0). The aminoxyl trapping reaction was more selective with a ratio of transcis addition of 4.41.0. Interestingly, when the benzoate group is axial, axial trapping by the sterically hindered aminoxyl is strongly favoured (axialequatorial = 7.41.0), whereas when the benzoate group is equatorial, there ...
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    The stereochemistry of addition of benzoyloxyl radicals to the conformationally rigid cyclohexene, trans-2-octalin, in the presence of the free radical scavenger 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxyl, is reported. Axial addition was favoured over equatorial addition with modest selectivity (axialequatorial = 1.71.0). The aminoxyl trapping reaction was more selective with a ratio of transcis addition of 4.41.0. Interestingly, when the benzoate group is axial, axial trapping by the sterically hindered aminoxyl is strongly favoured (axialequatorial = 7.41.0), whereas when the benzoate group is equatorial, there is only a small preference for equatorial trapping by the aminoxyl (equatorialaxial = 2.41.0). The structures of the four possible addition products were determined by 1H and 13C NMR spectroscopy, and confirmed in the case of the diaxial addition product [2(ax)-benzoyloxy-3(ax)-(1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-yloxy)-trans-decalin 3] by X-ray crystallographic analysis.
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    Journal Title
    Journal of the Chemical Society. Perkin Transactions 2
    Volume
    2000
    Publisher URI
    http://www.rsc.org/delivery/_ArticleLinking/ArticleLinking.cfm?JournalCode=P2&Year=2000&ManuscriptID=a908455j&Iss=4
    DOI
    https://doi.org/10.1039/A908455J
    Copyright Statement
    © 2000 Royal Society of Chemistry. This is the author-manuscript version of this paper. Please refer to the journal link for access to the definitive, published version.
    Subject
    History, heritage and archaeology
    Publication URI
    http://hdl.handle.net/10072/3448
    Collection
    • Journal articles

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