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    Direct determination of absolute configuration: a vibrational circular dichroism study on dimethyl-substituted phenyloxiranes synthesized by Shi epoxidation

    Access Status
    Fulltext not available
    Authors
    Fristrup, P.
    Lassen, P.
    Tanner, D.
    Jalkanen, Karl
    Date
    2008
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Fristrup, Peter and Lassen, Peter Rygaard and Tanner, David and Jalkanen, K. J.. 2008. Direct determination of absolute configuration: a vibrational circular dichroism study on dimethyl-substituted phenyloxiranes synthesized by Shi epoxidation. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta) 119: pp. 133-142.
    Source Title
    Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
    DOI
    10.1007/s00214-006-0186-1
    ISSN
    14322234
    Faculty
    Department of Applied Chemistry
    School of Science and Computing
    Faculty of Science and Engineering
    Remarks

    The original publication is available at : www.springerlink.com

    URI
    http://hdl.handle.net/20.500.11937/45018
    Collection
    • Curtin Research Publications
    Abstract

    The three possible dimethylsubstituted phenyloxiranes (cis, trans and geminal) were synthesized in both racemic (mCPBA) and enantiomerically enriched forms (Shi epoxidation) and subjected to a vibrational circular dichroism study. The experimental spectra were compared to theoretical spectra obtained using DFT/B3LYP calculations, and the differences between experiment and theory are discussed. The absolute configuration at the benzylic position was established as being (R), (S) and (R) for the cis, trans and geminal dimethylsubstituted phenyloxiranes, respectively. In all three cases the configuration of the major enantiomer was in accordance with a simple transition state model based on the spiro reaction mode.

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