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  • The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide

    Author(s)
    Loughlin, WA
    McCleary, MA
    Griffith University Author(s)
    Loughlin, Wendy A.
    Year published
    2003
    Metadata
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    Abstract
    The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 àin THF react with (ᩭphenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols 10-12, sulfonylbicyclo[5.2.0]nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide and upon oxidation with ...
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    The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 àin THF react with (ᩭphenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols 10-12, sulfonylbicyclo[5.2.0]nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide and upon oxidation with MCPBA, the cyclohexanone 4 and monoalkylated cyclobutanone 5 were obtained. The ratio of bicyclo[n.2.0]alkan-1-ol to alkylated products varied with the ketone enolate, conversion of phenyl vinyl sulfoxide, time, temperature and concentration of reaction and the stability and steric strain of the final bicyclo[n.2.0]alkan-1-ol product.
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    Journal Title
    Organic and Biomolecular Chemistry
    Volume
    1
    Publisher URI
    http://www.rsc.org/delivery/_ArticleLinking/ArticleLinking.cfm?JournalCode=OB&Year=2003&ManuscriptID=b208365e&Iss=8
    DOI
    https://doi.org/10.1039/B208365E
    Copyright Statement
    © 2003 Royal Society Reproduced in accordance with the copyright policy of the publisher. Use hypertext link for access to the journal's website.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/6317
    Collection
    • Journal articles

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