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

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Authors
Broden, Nicole
Advisor
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Date of Issue
2014-04-01
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Citation
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Title
Electrophilicity of Cu-bound Nitriles: Toward a Method for [2+2+2] Cyclizations
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Type
thesis
Description
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.
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Degree Awarded
Bachelor's
Semester
Spring
Department
Chemistry & Physics