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Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes

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Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes

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dc.contributor.author Bentabed-Ababsa, G. es_ES
dc.contributor.author Hamza-Reguig, S. es_ES
dc.contributor.author Derdour, A. es_ES
dc.contributor.author Domingo, L.R. es_ES
dc.contributor.author Sáez Cases, José Antonio es_ES
dc.contributor.author Roisnel, T. es_ES
dc.contributor.author Dorcet, V. es_ES
dc.contributor.author Nassar, E. es_ES
dc.contributor.author Mongin, F. es_ES
dc.date.accessioned 2016-01-29T10:52:07Z
dc.date.available 2016-01-29T10:52:07Z
dc.date.issued 2012
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10251/60355
dc.description.abstract [EN] The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoretically investigated using DFT methods in order to explain the reactivity and regioselectivity observed. es_ES
dc.description.sponsorship The authors thank Rennes Metropole and the Institut Universitaire de France for financial support to F. M. We are also grateful to the Spanish Government (project CTQ2009-11027/BQU).
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Organic and Biomolecular Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.title Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c2ob26442k
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2009-11027/ES/Estudios de reactividad en química orgánica/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Bentabed-Ababsa, G.; Hamza-Reguig, S.; Derdour, A.; Domingo, L.; Sáez Cases, JA.; Roisnel, T.; Dorcet, V.... (2012). Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes. Organic and Biomolecular Chemistry. 10(42):8434-8444. https://doi.org/10.1039/c2ob26442k es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c2ob26442k es_ES
dc.description.upvformatpinicio 8434 es_ES
dc.description.upvformatpfin 8444 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 10 es_ES
dc.description.issue 42 es_ES
dc.relation.senia 241469 es_ES
dc.identifier.pmid 23011385
dc.contributor.funder Ministerio de Ciencia e Innovación
dc.contributor.funder Institut Universitaire de France es_ES
dc.contributor.funder Rennes Metropole


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