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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
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Heteroaromatic Organocuprates
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No Insertion
dc.subject
Tmscl
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Otras Ciencias Químicas
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Ciencias Químicas
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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


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