{"id":{"repo_id":"mit","oai_identifier":"oai:dspace.mit.edu:1721.1/73390"},"canonical_url":"https://search.dev.ndltd.org/etd/mit/oai:dspace.mit.edu:1721.1/73390","repository":{"repo_id":"mit","name":"MIT","base_url":"https://dspace.mit.edu/oai/request"},"display":{"title":"Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes","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_html":"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_has_math":false,"creators":["Aguirre Kohnen, Amanda L. (Amanda Lucille)"],"institution":"Massachusetts Institute of Technology","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":"Massachusetts Institute of Technology. Dept. of Chemistry.","school":null,"contributors":[],"advisors":["Rick L. Danheiser."],"committee_chairs":[],"committee_members":[],"year":2012,"date_issued":"2012","date_published":"2012","updated_at":"2026-07-22T22:20:57Z","subjects":["Chemistry."],"languages":["eng"],"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."],"rights_urls":["http://dspace.mit.edu/handle/1721.1/7582"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/1721.1/73390","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Rick L. Danheiser."]},{"key":"dc:contributor.department","label":"Department","values":["Massachusetts Institute of Technology. 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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."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["S.M."]},{"key":"dc:title","label":"Title","values":["Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes"]}]}],"canonical_facts":{"dc:contributor.advisor":["Rick L. Danheiser."],"dc:contributor.department":["Massachusetts Institute of Technology. Dept. of Chemistry."],"dc:contributor.other":["Massachusetts Institute of Technology. Dept. of Chemistry."],"dc:creator":["Aguirre Kohnen, Amanda L. (Amanda Lucille)"],"dc:date.accessioned":["2012-09-27T15:28:10Z"],"dc:date.available":["2012-09-27T15:28:10Z"],"dc:date.issued":["2012"],"dc:description":["Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012.","Cataloged from PDF version of thesis.","Includes bibliographical references."],"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."],"dc:description.degree":["S.M."],"dc:identifier.uri":["http://hdl.handle.net/1721.1/73390"],"dc:language.iso":["eng"],"dc:publisher":["Massachusetts Institute of Technology"],"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."],"dc:rights.uri":["http://dspace.mit.edu/handle/1721.1/7582"],"dc:subject":["Chemistry."],"dc:title":["Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes"],"dc:type":["Thesis"]},"updated_at":"2026-07-22T22:20:57Z"}