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    Electrophilicity of Cu-bound Nitriles: Toward a Method for [2+2+2] Cyclizations

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    BrodenN_2014_Final.pdf (1.141Mb)
    Author
    Broden, Nicole
    Date of Issue
    2014-04-01
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    URI
    https://scholars.carroll.edu/handle/20.500.12647/156
    Title
    Electrophilicity of Cu-bound Nitriles: Toward a Method for [2+2+2] Cyclizations
    Type
    thesis
    Abstract
    Copper nitrile systems were explored to determine the change in nitrile nucleophilicity upon coordination to copper. Both Cu(I) and Cu(II) were explored. Complexes bearing electronwithdrawing nitriles and electron-donating nitriles were analyzed using FTIR spectroscopy. The findings that Cu(I) is more reactive than Cu(II) and that an electron-withdrawing functional group on the nitrile allows better coordination are being applied to determine conditions suitable for nitrile cyclotrimerization to generate triazines. Such a synthesis could provide a cheap and sustainable alternative transition metal for promoting cyclotrimerization reactions than is currently available. Another pathway to form a copper-bound intermediate to ultimately produce triazines is under investigation. A (Z)-4-(phenylamino)pent-3-en-2-one was formed from acetylacetone and aniline. This was subsequently reacted with copper to produce a copper-bound product.
    Degree Awarded
    Bachelor's
    Semester
    Spring
    Department
    Chemistry & Physics
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    • Chemistry and Physics Undergraduate Theses

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