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dc.contributor.author
Bouchet, Lydia María
dc.contributor.author
Peñeñory, Alicia Beatriz
dc.contributor.author
Robert, Marc
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Argüello, Juan Elias
dc.date.available
2018-04-24T21:10:01Z
dc.date.issued
2015-01
dc.identifier.citation
Bouchet, Lydia María; Peñeñory, Alicia Beatriz; Robert, Marc ; Argüello, Juan Elias; Breaking bonds with electrons: stepwise and concerted reductive cleavage of C–S, C–Se and Se–CN bonds in phenacylthiocyanates and phenacylselenocyanates; Royal Society of Chemistry; RSC Advances; 5; 16; 1-2015; 11753-11760
dc.identifier.issn
2046-2069
dc.identifier.uri
http://hdl.handle.net/11336/43397
dc.description.abstract
The mechanistic aspects of the electrochemical reduction of phenacylthio- and selenocyanates have been studied. With phenacylthiocyanates (1), a change in the reductive cleavage mechanism is observed as a function of the substituent on the phenyl ring. While a stepwise mechanism involving the intermediacy of a radical anion is followed for substrates bearing a strong electron withdrawing group, such as cyano and nitro substituent (1d, 1e), and a concerted mechanism is favoured for compounds bearing an electron-donating or no substituent on the phenyl ring (1a–c). A regioselective bond cleavage leads to the fragmentation of the CH2–S bond with all compounds 1a–e, further yielding the corresponding 1,4-diketone (3) as products. Contrastingly, with phenacylselenocyanates (2), two different reductive cleavages occur involving the breaking of both the CH2–Se and Se–CN bonds. Several products are obtained, all coming from nucleophilic attack at the α (phenacyl) carbon or the selenium atom.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Reduction
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Electrochemistry
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Sulphides
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Selenides
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Breaking bonds with electrons: stepwise and concerted reductive cleavage of C–S, C–Se and Se–CN bonds in phenacylthiocyanates and phenacylselenocyanates
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-04-24T19:31:47Z
dc.journal.volume
5
dc.journal.number
16
dc.journal.pagination
11753-11760
dc.journal.pais
Reino Unido
dc.description.fil
Fil: Bouchet, Lydia María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.description.fil
Fil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.description.fil
Fil: Robert, Marc. Université Paris Diderot - Paris 7; Francia
dc.description.fil
Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.journal.title
RSC Advances
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/c4ra16154h
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA16154H
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