Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes
Name
809806329-MIT.pdf
Description
Full printable version
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2.32 MB
Format
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Checksum (MD5)
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Author(s)
Aguirre Kohnen, Amanda L. (Amanda Lucille)
Advisor(s)
Rick L. Danheiser.
Date Issued
2012
Publisher
Massachusetts Institute of Technology
Abstract
Ynamides react with various classes of ketenes in intermolecular [2 + 2] cycloaddition to afford substituted cyclobutenones with complete regioselectivity. The cycloaddition substrates are easily assembled from amine derivatives by copper-catalyzed N-alkynylation with acetylenic bromides. The alkynylation reaction provides access to thermally sensitive compounds such as diynamides. Synthesis of the requisite halo diynes is achieved by Sonogashira coupling followed by base-mediated elimination at low temperature.
Description
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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