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    Practical synthesis and reactivity of [3]dendralene

    Access Status
    Fulltext not available
    Authors
    Bradford, T.
    Payne, Alan
    Willis, A.
    Paddon-Row, M.
    Sherburn, M.
    Date
    2010
    Type
    Journal Article
    
    Metadata
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    Citation
    Bradford, Tanya A. and Payne, Alan D. and Willis, Anthony C. and Paddon-Row, Michael N. and Sherburn, Michael S. 2010. Practical synthesis and reactivity of [3]dendralene. Journal of Organic Chemistry 75 (2): pp. 491-494.
    Source Title
    Journal of Organic Chemistry
    DOI
    10.1021/jo9024557
    ISSN
    00223263
    URI
    http://hdl.handle.net/20.500.11937/6896
    Collection
    • Curtin Research Publications
    Abstract

    A convenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diets-Alder reactivity of [3]dendralene-including double cycloaddition sequences and catalytic enantio selective variant-are reported.

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