2026-09-20T02:38:51Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/733902022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131023
Rick L. Danheiser.
Aguirre Kohnen, Amanda L. (Amanda Lucille)
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2012-09-27T15:28:10Z
2012-09-27T15:28:10Z
2012
2012
http://hdl.handle.net/1721.1/73390
809806329
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012.
Cataloged from PDF version of thesis.
Includes bibliographical references.
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.
by Amanda L. Aguirre Kohnen.
S.M.
57 p.
eng
Massachusetts Institute of Technology
M.I.T. theses are protected by
copyright. They may be viewed from this source for any purpose, but
reproduction or distribution in any format is prohibited without written
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http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes
Thesis
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Publication
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<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.</Abstract>
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