A theoretical study of the Duff reaction : insights into its selectivity

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dc.citation.titleOrganic and Biomolecular Chemistryes
dc.citation.volume14(44)es
dc.creatorGrimblat, Nicolás
dc.creatorSarotti, Ariel Marcelo
dc.creatorKaufman, Teodoro Saúl
dc.creatorSimonetti, Sebastián Osvaldo
dc.date.accessioned2018-02-02T19:28:55Z
dc.date.available2018-02-02T19:28:55Z
dc.date.issued2016-10-07
dc.descriptionThe Duff reaction is one of the most employed methods for the ortho-formylation of phenols; however, not much is truly known about its mechanism. Using DFT calculations, we disclose the first theoretical study regarding the selectivity-determining step of the reaction. We have found that this stage is governed by a hydrogen bond, that gives rise to a cyclohexa-2,4-dienone intermediate and establishes the position where the formylation will take place. These findings were evaluated by analysis of the reaction outcome of several non-symmetrically substituted phenols.es
dc.description.filFil: Grimblat, Nicolás. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Sarotti, Ariel Marcelo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Simonetti, Sebastián Osvaldo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica (ANPCyT), PICT-2012-0970 y PICT-2014-0445es
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET)es
dc.formatapplication/pdf
dc.format.extent10496-10501es
dc.identifier.issn1477-0520es
dc.identifier.urihttp://hdl.handle.net/2133/10491
dc.language.isoenges
dc.publisherRoyal Society of Chemistryes
dc.relation.publisherversionhttp://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob01887d#!divAbstractes
dc.relation.publisherversiondoi:10.1039/C6OB01887Des
dc.rightsopenAccesses
dc.rights.holderGrimblat, Nicoláses
dc.rights.holderSarotti, Ariel Marceloes
dc.rights.holderKaufman, Teodoro Saúles
dc.rights.holderSimonetti, Sebastián Osvaldoes
dc.rights.holderRoyal Society of Chemistryes
dc.rights.holderUniversidad Nacional de Rosarioes
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/ar/*
dc.subjectDuff Reactiones
dc.subjectOrtho-formylation of Phenolses
dc.subjectDFT Calculationses
dc.subjectHydrogen Bondes
dc.subjectNon-symmetrically Substituted Phenolses
dc.titleA theoretical study of the Duff reaction : insights into its selectivityes
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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