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

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dc.creator Grimblat, Nicolás
dc.creator Sarotti, Ariel Marcelo
dc.creator Kaufman, Teodoro Saúl
dc.creator Simonetti, Sebastián Osvaldo
dc.date.accessioned 2018-02-02T19:28:55Z
dc.date.available 2018-02-02T19:28:55Z
dc.date.issued 2016-10-07
dc.identifier.issn 1477-0520 es
dc.identifier.uri http://hdl.handle.net/2133/10491
dc.description The 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.sponsorship Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT), PICT-2012-0970 y PICT-2014-0445 es
dc.description.sponsorship Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) es
dc.format application/pdf
dc.format.extent 10496-10501 es
dc.language.iso eng es
dc.publisher Royal Society of Chemistry es
dc.rights openAccess es
dc.rights.uri http://creativecommons.org/licenses/by-nc-sa/2.5/ar/ *
dc.subject Duff Reaction es
dc.subject Ortho-formylation of Phenols es
dc.subject DFT Calculations es
dc.subject Hydrogen Bond es
dc.subject Non-symmetrically Substituted Phenols es
dc.title A theoretical study of the Duff reaction : insights into its selectivity es
dc.type article
dc.type artículo
dc.type publishedVersion
dc.rights.holder Grimblat, Nicolás es
dc.rights.holder Sarotti, Ariel Marcelo es
dc.rights.holder Kaufman, Teodoro Saúl es
dc.rights.holder Simonetti, Sebastián Osvaldo es
dc.rights.holder Royal Society of Chemistry es
dc.rights.holder Universidad Nacional de Rosario es
dc.relation.publisherversion http://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob01887d#!divAbstract es
dc.relation.publisherversion doi:10.1039/C6OB01887D es
dc.citation.title Organic and Biomolecular Chemistry es
dc.citation.volume 14(44) es
dc.description.fil Fil: Grimblat, Nicolás. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Sarotti, Ariel Marcelo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.description.fil Fil: Simonetti, Sebastián Osvaldo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. es
dc.type.collection articulo
dc.type.version publishedVersion es


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