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dc.contributor.author Rodriguez, Cristian Ramon
dc.contributor.author Vazquez, Alvaro Joaquin
dc.contributor.author Sbarbati, Norma Ethel
dc.date.available 2019-01-08T21:08:06Z
dc.date.issued 2010-10
dc.identifier.citation Rodriguez, Cristian Ramon; Vazquez, Alvaro Joaquin; Sbarbati, Norma Ethel; A wide mechanistic spectrum observed in three different reactions with organometallic reagents; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 23; 10; 10-2010; 978-984
dc.identifier.issn 0894-3230
dc.identifier.uri http://hdl.handle.net/11336/67732
dc.description.abstract The halogen-lithium exchange reaction is of one of the most powerful method for the preparation of organolithium compounds, but its mechanism is still controversial. To afford some new elements, we synthesized a new suitable fast radical clock, bearing a phenyl group at the alkene C-terminal. The examination of some mechanistic clues, as well as the identification of the unexpected by-products allowed the conclusion that the reaction proceeds by a polar mechanism and no evidence for radicals were found. The second reaction discussed is the insertion of NO in the N-Li bond of lithium amides. Evidence for the involving of paramagnetic and nitrosonium intermediates, as well as equilibria between different reactive species were essential for the proposal of a whole complex mechanism, which was confirmed by theoretical calculations. Finally, results on the addition of heteroaromatic organocuprates to a,b-unsaturated substrates are presented. Several reaction conditions were looked for to lead the reaction toward the more interesting 1,4-conjugated addition. Thus, addition of up to 6 equivalents of TMSCl to the reaction with arylcuprates leads to a clean addition yielding more than 95% of the 1,4-addition product. A further objective of the paper is to show how the search of unexpected routes of reaction allowed developing original pathways to lead them toward the formation of appealing functionalized compounds. Copyright © 2010 John Wiley and Sons, Ltd.
dc.format application/pdf
dc.language.iso eng
dc.publisher John Wiley & Sons Ltd
dc.rights info:eu-repo/semantics/restrictedAccess
dc.rights.uri https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject HALOGEN-LITHIUM EXCHANGE
dc.subject HETEROAROMATIC ORGANOCUPRATES
dc.subject NO INSERTION
dc.subject TMSCL
dc.subject.classification Otras Ciencias Químicas
dc.subject.classification Ciencias Químicas
dc.subject.classification CIENCIAS NATURALES Y EXACTAS
dc.title A wide mechanistic spectrum observed in three different reactions with organometallic reagents
dc.type info:eu-repo/semantics/article
dc.type info:ar-repo/semantics/artículo
dc.type info:eu-repo/semantics/publishedVersion
dc.date.updated 2019-01-07T13:56:22Z
dc.journal.volume 23
dc.journal.number 10
dc.journal.pagination 978-984
dc.journal.pais Reino Unido
dc.journal.ciudad Londres
dc.description.fil Fil: Rodriguez, Cristian Ramon. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
dc.description.fil Fil: Vazquez, Alvaro Joaquin. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
dc.description.fil Fil: Sbarbati, Norma Ethel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.journal.title Journal Of Physical Organic Chemistry
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1761
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1002/poc.1761
dc.conicet.fuente individual


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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)