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  • Diversion from bicyclo[4.2.0]octanol formation through the use of vinyl electrophiles

    Author(s)
    Loughlin, WA
    Rowen, CC
    Healy, PC
    Griffith University Author(s)
    Healy, Peter C.
    Loughlin, Wendy A.
    Rowen, Catherine C.
    Year published
    2005
    Metadata
    Show full item record
    Abstract
    Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.
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    Journal Title
    Synthesis: journal of synthetic organic chemistry
    Volume
    13
    Publisher URI
    http://www.thieme-chemistry.com/en/products/journals/synthesis.html
    DOI
    https://doi.org/10.1055/s-2005-869993
    Copyright Statement
    © 2005 Georg Thieme Verlag. Please refer to the journal link for access to the definitive, published version.
    Subject
    Analytical chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/4957
    Collection
    • Journal articles

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