Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism

Autores
Oksdath Mansilla, Gabriela; Peñeñory, Alicia Beatriz
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The reactions of 2-(4-Z-phenyl)-1,3-dithiane anions (Z=H, OMe, Cl, CN) with neopentyl, neophyl and phenyl iodides were studied in DMSO, taking into consideration the effect of the Z substituent on the dithiane anions reactivity as well as on the product distribution. These substitution reactions proceed by an SRN1 mechanism with radicals and radical anions as intermediates. Two competitive pathways are possible for the radical anion of the substitution product, namely electron transfer (ET) to the substrate giving the substitution product and C-S bond fragmentation to yield a distonic radical anion. ET is the main pathway for the reactions between dithiane anions bearing electron-donor substituents and neopentyl or its analogue iodides affording the substitution products in moderate yields (41-53%). Copyright © 2011 John Wiley & Sons, Ltd.
Fil: Oksdath Mansilla, Gabriela. 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
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
Materia
Dithiane Anion
Electron Transfer
Fragmentation
Radical
Radical Anion
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/62217
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanismOksdath Mansilla, GabrielaPeñeñory, Alicia BeatrizDithiane AnionElectron TransferFragmentationRadicalRadical Anionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The reactions of 2-(4-Z-phenyl)-1,3-dithiane anions (Z=H, OMe, Cl, CN) with neopentyl, neophyl and phenyl iodides were studied in DMSO, taking into consideration the effect of the Z substituent on the dithiane anions reactivity as well as on the product distribution. These substitution reactions proceed by an SRN1 mechanism with radicals and radical anions as intermediates. Two competitive pathways are possible for the radical anion of the substitution product, namely electron transfer (ET) to the substrate giving the substitution product and C-S bond fragmentation to yield a distonic radical anion. ET is the main pathway for the reactions between dithiane anions bearing electron-donor substituents and neopentyl or its analogue iodides affording the substitution products in moderate yields (41-53%). Copyright © 2011 John Wiley & Sons, Ltd.Fil: Oksdath Mansilla, Gabriela. 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; ArgentinaFil: 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; ArgentinaJohn Wiley & Sons Ltd2011-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62217Oksdath Mansilla, Gabriela; Peñeñory, Alicia Beatriz; Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 24; 12; 12-2011; 1136-11430894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1837info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1837info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:45:58Zoai:ri.conicet.gov.ar:11336/62217instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:45:58.994CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
title Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
spellingShingle Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
Oksdath Mansilla, Gabriela
Dithiane Anion
Electron Transfer
Fragmentation
Radical
Radical Anion
title_short Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
title_full Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
title_fullStr Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
title_full_unstemmed Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
title_sort Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism
dc.creator.none.fl_str_mv Oksdath Mansilla, Gabriela
Peñeñory, Alicia Beatriz
author Oksdath Mansilla, Gabriela
author_facet Oksdath Mansilla, Gabriela
Peñeñory, Alicia Beatriz
author_role author
author2 Peñeñory, Alicia Beatriz
author2_role author
dc.subject.none.fl_str_mv Dithiane Anion
Electron Transfer
Fragmentation
Radical
Radical Anion
topic Dithiane Anion
Electron Transfer
Fragmentation
Radical
Radical Anion
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The reactions of 2-(4-Z-phenyl)-1,3-dithiane anions (Z=H, OMe, Cl, CN) with neopentyl, neophyl and phenyl iodides were studied in DMSO, taking into consideration the effect of the Z substituent on the dithiane anions reactivity as well as on the product distribution. These substitution reactions proceed by an SRN1 mechanism with radicals and radical anions as intermediates. Two competitive pathways are possible for the radical anion of the substitution product, namely electron transfer (ET) to the substrate giving the substitution product and C-S bond fragmentation to yield a distonic radical anion. ET is the main pathway for the reactions between dithiane anions bearing electron-donor substituents and neopentyl or its analogue iodides affording the substitution products in moderate yields (41-53%). Copyright © 2011 John Wiley & Sons, Ltd.
Fil: Oksdath Mansilla, Gabriela. 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
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
description The reactions of 2-(4-Z-phenyl)-1,3-dithiane anions (Z=H, OMe, Cl, CN) with neopentyl, neophyl and phenyl iodides were studied in DMSO, taking into consideration the effect of the Z substituent on the dithiane anions reactivity as well as on the product distribution. These substitution reactions proceed by an SRN1 mechanism with radicals and radical anions as intermediates. Two competitive pathways are possible for the radical anion of the substitution product, namely electron transfer (ET) to the substrate giving the substitution product and C-S bond fragmentation to yield a distonic radical anion. ET is the main pathway for the reactions between dithiane anions bearing electron-donor substituents and neopentyl or its analogue iodides affording the substitution products in moderate yields (41-53%). Copyright © 2011 John Wiley & Sons, Ltd.
publishDate 2011
dc.date.none.fl_str_mv 2011-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/62217
Oksdath Mansilla, Gabriela; Peñeñory, Alicia Beatriz; Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 24; 12; 12-2011; 1136-1143
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62217
identifier_str_mv Oksdath Mansilla, Gabriela; Peñeñory, Alicia Beatriz; Reactivity of 2-aryl-1,3-dithiane anions towards neopentyl, neophyl and phenyl iodides. New evidence for an SRN1 mechanism; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 24; 12; 12-2011; 1136-1143
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1837
info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1837
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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