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

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