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    Distal functionalisation of C4symmetric tetramethoxyresorcinarene by selective lithiation

    Access Status
    Fulltext not available
    Authors
    Tan, D.
    Mocerino, Mauro
    Date
    2018
    Type
    Journal Article
    
    Metadata
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    Citation
    Tan, D. and Mocerino, M. 2018. Distal functionalisation of C4symmetric tetramethoxyresorcinarene by selective lithiation. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry. 91 (1-2): pp. 71-80.
    Source Title
    Journal of Inclusion Phenomena and Molecular Recognition in Chemistry
    DOI
    10.1007/s10847-018-0802-4
    ISSN
    0923-0750
    School
    School of Molecular and Life Sciences (MLS)
    URI
    http://hdl.handle.net/20.500.11937/68858
    Collection
    • Curtin Research Publications
    Abstract

    © 2018, Springer Science+Business Media B.V., part of Springer Nature. Three novel C4symmetric O-substituted derivatives of tetramethoxyresorcinarene were synthesised and characterised and the selective distal lithiation of these derivatives was investigated. Lithiation of the tetraethoxy derivative, followed by quenching with dimethyldisulfide selectively afforded the distal product in 36% yield after removal of unreacted starting resorcinarene. Lithiation of the MOM derivative produced the five possible lithiated products, with the mono being the major product; the distally substituted derivative being a minor product. The benzyloxyresorcinarene appeared to be unstable under the lithation conditions. These results suggest that the selectivity of the distal lithation reaction is heavily dependent on the O-substituents of the resorcinarene.

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