Curtin University Homepage
  • Library
  • Help
    • Admin

    espace - Curtin’s institutional repository

    JavaScript is disabled for your browser. Some features of this site may not work without it.
    View Item 
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item

    Mannich and O-Alkylation Reactions of Tetraalkoxyresorcin[4]arenes. The Use of Some Products in Ligand-Assisted Reactions

    Access Status
    Fulltext not available
    Authors
    Buckley, B.
    Boxhall, J.
    Page, P.
    Chan, Y.
    Elsegood, M.
    Heaney, H.
    Holmes, K.
    Mcildowie, M.
    McKee, V.
    McGarth, M.
    Mocerino, Mauro
    Poulton, A.
    Sampler, E.
    Skelton, B.
    White, A.
    Date
    2006
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Buckley, Benjamin and Boxhall, Jonathan and Page, Philip and Chan, Yohan and Elsegood, Mark and Heaney, Harry and Holmes, Kathryn and Mcildowie, Matthew and McKee, Vickie and McGrath, Matthew and Mocerino, Mauro and Poulton, Andrew and Sampler, Edward and Skelton, Brian and White, Allan. 2006. Mannich and O-Alkylation Reactions of Tetraalkoxyresorcin[4]arenes. The Use of Some Products in Ligand-Assisted Reactions. European Journal of Organic Chemistry 2006 (22): 5117-5134.
    Source Title
    European Journal of Organic Chemistry
    DOI
    10.1002/ejoc.200601032
    Faculty
    Research Centres
    Curtin
    Centre for Applied Organic Geochemistry
    Centres of Excellence
    School
    Nanochemistry Research Institute, Curtin University of Technology
    Remarks

    2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Please refer to the publisher for the definitive version.

    as the corrected version (Volume 2007, Issue 7 , Pages 1203 - 1203)

    URI
    http://hdl.handle.net/20.500.11937/4752
    Collection
    • Curtin Research Publications
    Abstract

    The measurement of the pKa of racemic tetramethoxyresorcin[4]arenes explains the failure to obtain good yields in attempted Mannich reactions of these substrates under classical reaction conditions. The failure is related to the lack of adequate concentrations of the iminium ions that results from the reduced acid strength of tetraalkoxyresorcin[4]arenes compared with that of the parent octahydroxyresorcin[4]arenes. However, the preparation of a series of Mannich bases derived from racemic tetraalkoxyresorcin[4]arenes was accomplished under microwave-assisted aprotic reaction conditions and the use of preformed iminium ion intermediates. When the reactions were carried out with the use of chiral bis(aminol) ethers, mixtures of diastereomers were obtained that could be separated by flash chromatography. The absolute configurations of the enantiomerically pure tetrabenzoxazine derivatives were established in some cases by X-ray crystallographic analysis and by a comparison of the nuclear magnetic resonance spectroscopic data. The alkylation of racemic tetramethoxyresorcin[4]arenes was achieved with the use of an excess of 2-bromo-N-[(R)-(+)-(a-methylbenzyl)] acetamide in acetonitrile containing potassium carbonate. Enantioselective ligand-assisted reactions of aromatic aldehydes are also reported with the use of dialkylzinc reagents both in the absence and in the presence of terminal alkynes.

    Related items

    Showing items related by title, author, creator and subject.

    • The Preparation and Absolute Configurations of Enantiomerically Pure C4-Symmetric Tetraalkoxyresorcin[4]arenes Obtained from Camphorsulfonate Derivatives
      Buckley, B.; Page, P.; Chan, Y.; Heaney, H.; Klaes, M.; Mcildowie, Matthew; McKee, V.; Mattay, J.; Mocerino, Mauro; Moreno, E.; Skelton, B.; White, A. (2006)
      The preparation of a series of diastereoisomeric tetracamphorsulfonates derived from racemic tetramethoxyresorcin[4]arenes was achieved by reactions with an excess of (S)-(+)-10-camphorsulfonyl chloride in pyridine followed ...
    • The Preparation and Absolute Configurations of Enantiomerically Pure C4-Symmetric Tetraalkoxyresorcin[4]arenes Obtained from Camphorsulfonate Derivatives
      Buckley, B.; Page, P.; Chan, Y.; Heaney, H.; Klaes, M.; Mcildowie, M.; McKee, V.; Mattay, J.; Mocerino, Mauro; Moreno, E.; Skelton, B.; White, A. (2006)
      The preparation of a series of diastereoisomeric tetracamphorsulfonates derived from racemic tetramethoxyresorcin[4]arenes was achieved by reactions with an excess of (S)‐(+)‐10‐camphorsulfonyl chloride in pyridine followed ...
    • Mannich and O-Alkylation Reactions of Tetraalkoxyresorcin[4]arenes - The Use of Some Products in Ligand-Assisted Reactions
      Buckley, B.; Boxhall, J.; Page, P.; Chan, Y.; Elsegood, M.; Heaney, H.; Holmes, K.; Mcildowie, Matthew; McKee, V.; McGrath, M.; Mocerino, Mauro; Poulton, A.; Sampler, E.; Skelton, B.; White, A. (2006)
      The measurement of the pKa of racemic tetramethoxyresorcin[4]arenes explains the failure to obtain good yields in attempted Mannich reactions of these substrates under classical reaction conditions. The failure is related ...
    Advanced search

    Browse

    Communities & CollectionsIssue DateAuthorTitleSubjectDocument TypeThis CollectionIssue DateAuthorTitleSubjectDocument Type

    My Account

    Admin

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    Follow Curtin

    • 
    • 
    • 
    • 
    • 

    CRICOS Provider Code: 00301JABN: 99 143 842 569TEQSA: PRV12158

    Copyright | Disclaimer | Privacy statement | Accessibility

    Curtin would like to pay respect to the Aboriginal and Torres Strait Islander members of our community by acknowledging the traditional owners of the land on which the Perth campus is located, the Whadjuk people of the Nyungar Nation; and on our Kalgoorlie campus, the Wongutha people of the North-Eastern Goldfields.