A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study

Autores
Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; González, Mercedes; Cerecetto, Hugo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with á-haloketones, in the presence of excess of potassium iodide, has been observed. Instead of the expected reaction of the nucleophile in a remote point of the molecule, we have obtained a product resulted from the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2-dithiole. In order to obtain an efficient protocol in terms of energy efficiency, this methodology was studied under conventional and microwave heating with similar or better results in the latter conditions. Simplicity and great efficiency in this one-step transformation are some of the advantages of this reaction. Moreover, the results can be explained according to the Pearsons hard and soft acid base theory.
Fil: Couto, Marcos. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Cabrera, Mauricio. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: González, Mercedes. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Cerecetto, Hugo. Universidad de la República. Facultad de Ciencias; Uruguay
Materia
3h-1,2-Dithiole-3-Thione
(E)-3-Alkylidene-3h-1,2-Dithiole
Dft Calculations
Hsab Theory
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:11336/23735
Acceder
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network_name_str CONICET Digital (CONICET)
spelling A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical studyCouto, MarcosCabrera, MauricioEcheverría, Gustavo AlbertoPiro, Oscar EnriqueGonzález, MercedesCerecetto, Hugo3h-1,2-Dithiole-3-Thione(E)-3-Alkylidene-3h-1,2-DithioleDft CalculationsHsab Theoryhttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with á-haloketones, in the presence of excess of potassium iodide, has been observed. Instead of the expected reaction of the nucleophile in a remote point of the molecule, we have obtained a product resulted from the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2-dithiole. In order to obtain an efficient protocol in terms of energy efficiency, this methodology was studied under conventional and microwave heating with similar or better results in the latter conditions. Simplicity and great efficiency in this one-step transformation are some of the advantages of this reaction. Moreover, the results can be explained according to the Pearsons hard and soft acid base theory.Fil: Couto, Marcos. Universidad de la República. Facultad de Ciencias; UruguayFil: Cabrera, Mauricio. Universidad de la República. Facultad de Ciencias; UruguayFil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: González, Mercedes. Universidad de la República. Facultad de Ciencias; UruguayFil: Cerecetto, Hugo. Universidad de la República. Facultad de Ciencias; UruguaySpringer2014-01info: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/11336/23735Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; González, Mercedes; et al.; A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study; Springer; Molecular Diversity; 18; 2; 1-2014; 285-2941381-19911573-501XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007/s11030-013-9499-xinfo:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-013-9499-xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:43:46Zoai:ri.conicet.gov.ar:11336/23735instacron: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:34982025-09-03 09:43:46.992CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
title A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
spellingShingle A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
Couto, Marcos
3h-1,2-Dithiole-3-Thione
(E)-3-Alkylidene-3h-1,2-Dithiole
Dft Calculations
Hsab Theory
title_short A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
title_full A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
title_fullStr A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
title_full_unstemmed A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
title_sort A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study
dc.creator.none.fl_str_mv Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
author Couto, Marcos
author_facet Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
author_role author
author2 Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 3h-1,2-Dithiole-3-Thione
(E)-3-Alkylidene-3h-1,2-Dithiole
Dft Calculations
Hsab Theory
topic 3h-1,2-Dithiole-3-Thione
(E)-3-Alkylidene-3h-1,2-Dithiole
Dft Calculations
Hsab Theory
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.3
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with á-haloketones, in the presence of excess of potassium iodide, has been observed. Instead of the expected reaction of the nucleophile in a remote point of the molecule, we have obtained a product resulted from the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2-dithiole. In order to obtain an efficient protocol in terms of energy efficiency, this methodology was studied under conventional and microwave heating with similar or better results in the latter conditions. Simplicity and great efficiency in this one-step transformation are some of the advantages of this reaction. Moreover, the results can be explained according to the Pearsons hard and soft acid base theory.
Fil: Couto, Marcos. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Cabrera, Mauricio. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: González, Mercedes. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Cerecetto, Hugo. Universidad de la República. Facultad de Ciencias; Uruguay
description In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with á-haloketones, in the presence of excess of potassium iodide, has been observed. Instead of the expected reaction of the nucleophile in a remote point of the molecule, we have obtained a product resulted from the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2-dithiole. In order to obtain an efficient protocol in terms of energy efficiency, this methodology was studied under conventional and microwave heating with similar or better results in the latter conditions. Simplicity and great efficiency in this one-step transformation are some of the advantages of this reaction. Moreover, the results can be explained according to the Pearsons hard and soft acid base theory.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/23735
Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; González, Mercedes; et al.; A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study; Springer; Molecular Diversity; 18; 2; 1-2014; 285-294
1381-1991
1573-501X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/23735
identifier_str_mv Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; González, Mercedes; et al.; A serendipitous conversion in one step of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study; Springer; Molecular Diversity; 18; 2; 1-2014; 285-294
1381-1991
1573-501X
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://link.springer.com/article/10.1007/s11030-013-9499-x
info:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-013-9499-x
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 Springer
publisher.none.fl_str_mv Springer
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 13.13397

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