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Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes

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dc.contributor.advisor Rick L. Danheiser. en_US
dc.contributor.author Aguirre Kohnen, Amanda L. (Amanda Lucille) en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.date.accessioned 2012-09-27T15:28:10Z
dc.date.available 2012-09-27T15:28:10Z
dc.date.copyright 2012 en_US
dc.date.issued 2012 en_US
dc.identifier.uri http://hdl.handle.net/1721.1/73390
dc.description Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012. en_US
dc.description Cataloged from PDF version of thesis. en_US
dc.description Includes bibliographical references. en_US
dc.description.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. en_US
dc.description.statementofresponsibility by Amanda L. Aguirre Kohnen. en_US
dc.format.extent 57 p. en_US
dc.language.iso eng en_US
dc.publisher Massachusetts Institute of Technology en_US
dc.rights 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 permission. See provided URL for inquiries about permission. en_US
dc.rights.uri http://dspace.mit.edu/handle/1721.1/7582 en_US
dc.subject Chemistry. en_US
dc.title Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes en_US
dc.type Thesis en_US
dc.description.degree S.M. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.identifier.oclc 809806329 en_US


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