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    Synthesis of silyloxyacrolein for [4+3] cycloaddition and preparation of carbonate closomer

    Liu, Yuan, 1979-
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    Date
    2008
    Format
    Thesis
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    Abstract
    [ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT AUTHOR'S REQUEST.] Followed by Funk's method, I synthesized silyloxyacroleins and used them as dienophiles to react with different dienes in [4+3] cycloaddition reaction. These enals such as 2-(tert-butyldimethylsilyloxy)-hept-2-eanl can undergo [4 + 3] cyclizations with different dienes in the presence of Lewis acids or Bronsted acid with excellent regio- and stereoselectivity. The reaction conditions for the synthesis dodecacarbonate-closo-dodecaborate were optimized. This carbonate closomer can be used in a drug delivery system. The stability of this dodecacarbonate-closo-dodecaborate was examined: it is stable in acid environment, but can be decomposed into 4-nitrophenol gradually in basic solutions. The solubility of this carbonate closomer was also investigated: it does not dissolve in water, but has a good solubility in diethyl ether and toluene.
    URI
    https://hdl.handle.net/10355/6114
    https://doi.org/10.32469/10355/6114
    Degree
    M.S.
    Thesis Department
    Chemistry (MU)
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    Access is limited to the campuses of the University of Missouri.
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    • 2008 MU theses - Access restricted to UM
    • Chemistry electronic theses and dissertations (MU)

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