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dc.contributor.authorBélanger, Guillaumefr
dc.contributor.authorLévesque, Françoisfr
dc.contributor.authorPâquet, Juliefr
dc.contributor.authorBarbe, Guillaumefr
dc.contributor.editorUniversité de Sherbrooke. Laboratoire de synthèse organique et de développement de stratégies de synthèsefr
dc.date.accessioned2020-08-24T20:40:36Z
dc.date.available2020-08-24T20:40:36Z
dc.date.created2005fr
dc.date.issued2020-08-24
dc.identifier.urihttp://hdl.handle.net/11143/17288
dc.description.abstractAbstract: In the course of developing a new synthetic methodology using ketenes in sequential cycloaddition steps, we were faced with a competition problem with molecules containing a ketene tethered to more than one reacting partner. To pinpoint the electronic and tethering requirements for a chemoselective reaction, we undertook a series of ketene−alkene [2 + 2] cycloaddition competition experiments. Those experiments were conducted on molecules containing either two identical alkenes having different tether lengths or two alkenes having the same tether length but being electronically different. We demonstrated that the reaction is much faster for forming five-membered rings than six-membered rings and calculated the Hammett constant ρ for intramolecular ketene−alkene [2 + 2] cycloadditions to be −1.39.fr
dc.language.isoengfr
dc.relation.isformatofhttps://doi.org/10.1021/jo0483466fr
dc.relation.ispartofISSN:1520-6904fr
dc.relation.ispartofJournal of Organic Chemistryfr
dc.rightsAttribution - Pas d’Utilisation Commerciale - Pas de Modification 2.5 Canada*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/2.5/ca/*
dc.subjectHydrocarbonsfr
dc.subjectAnionsfr
dc.subjectCyclizationfr
dc.subjectAddition reactionsfr
dc.subjectSubstituentsfr
dc.titleCompetition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: What does it take to win?fr
dc.typeArticlefr
dc.rights.holder© ACS Journal Publishingfr
udes.description.typestatusPost-publicationfr
udes.description.typepubRévisé et accepté par des pairsfr
udes.description.pages291-296fr
udes.description.period70(1)fr
udes.description.diffusionDiffusé par Savoirs UdeS, le dépôt institutionnel de l'Université de Sherbrookefr
dc.identifier.bibliographicCitationBélanger, G., Lévesque, F., Pâquet, J., et Barbe, G. (2005). "Competition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: What does it take to win?" Journal of Organic Chemistry, 70(1), 291-296. https://doi.org/10.1021/jo0483466fr
udes.description.sourceJournal of Organic Chemistryfr
udes.autorisation.depottruefr
udes.description.ordreauteursBélanger, Guillaume; Lévesque, François; Pâquet, Julie; Barbe, Guillaumefr


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Attribution - Pas d’Utilisation Commerciale - Pas de Modification 2.5 Canada
Except where otherwise noted, this document's license is described as Attribution - Pas d’Utilisation Commerciale - Pas de Modification 2.5 Canada