Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides

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dc.citation.titleRSC Advanceses
dc.citation.volume7(75)es
dc.creatorPorta, Exequiel Oscar Jesús
dc.creatorVallejos, Margarita M.
dc.creatorBracca, Andrea Beatriz Juana
dc.creatorLabadie, Guillermo Roberto
dc.date.accessioned2021-02-12T17:29:11Z
dc.date.available2021-02-12T17:29:11Z
dc.date.issued2017-10-10
dc.description[3,3]-Sigmatropic rearrangement of isoprenyl azides has been extensively investigated in an experimental and theoretical level. Prenylazides with different chain lengths and phenyl prenylazide have been synthesized. NMR analysis of each azide has been made to determine the equilibrium composition, showing the predominance of primary allyl azides over the tertiary ones and E over Z isomer, regardless of the chain length, temperature, solvent or the regiochemistry of the precursor isoprenyl alcohol. It was determined that phenyl prenylazides do not experience [3,3]-sigmatropic rearrangement. In order to rationalize the experimental results and to gain insight in the mechanism of the [3,3]-sigmatropic rearrangement of prenylazides a theoretical study was performed using density functional theory and the QTAIM approach.es
dc.descriptionThis is a post-peer-review, pre-copyedit version of an article published in RSC Advances. The final authenticated version is available online at: https://doi.org/10.1039/c7ra09759j
dc.description.filFil: Porta, Exequiel O. J. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR -CONICET); Argentina.es
dc.description.filFil: Vallejos, Margarita M. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas, Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino. Laboratorio de Química Orgánica (IQUIBA-NEA CONICET); Argentina.es
dc.description.filFil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR -CONICET); Argentina.es
dc.description.filFil: Labadie, Guillermo Roberto. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR -CONICET); Argentina.es
dc.description.filFil: Labadie, Guillermo Roberto. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina.es
dc.description.sponsorshipUniversidad Nacional de Rosario (UNR)es
dc.description.sponsorshipFundación Josefina Pratses
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas de Argentina (CONICET): PIP 2009-11/0796 and PIP 2012-14/0448es
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica: PICT-2011-0589, PICT 2015-2635es
dc.description.sponsorshipSECYT-UNNE: PI F005-2013es
dc.description.sponsorshipUNICEF/UNDP/WORLD BANK/WHO Special Programme for Research and Training in Tropical Diseaseses
dc.formatapplication/pdf
dc.format.extent47527-47538es
dc.identifier.issn2046-2069es
dc.identifier.urihttp://hdl.handle.net/2133/19641
dc.language.isoenges
dc.publisherRoyal Society of Chemistryes
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2017/RA/C7RA09759J#!divAbstractes
dc.relation.publisherversionhttps://doi.org/10.1039/c7ra09759jes
dc.rightsopenAccesses
dc.rights.holderRoyal Society of Chemistryes
dc.rights.holderUniversidad Nacional de Rosario
dc.rights.textAttribution 3.0 Unported (CC BY 3.0)es
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/*
dc.subjectReacciones Pericíclicases
dc.subjectReordenamiento Sigmatropicoes
dc.subjectPrenilazidases
dc.titleExperimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azideses
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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