A serendipitous one-step conversion 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 α-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 Pearson's hard and soft acid base theory.
Facultad de Ciencias Exactas
Materia
Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/133530
Acceder
id SEDICI_889e7ff6e6b68b0dfde2e58620157977
oai_identifier_str oai:sedici.unlp.edu.ar:10915/133530
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling A serendipitous one-step conversion 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, HugoQuímica3H-1,2-Dithiole-3-thione(E)-3-Alkylidene3H-1,2-dithioleDFT calculationsHSAB theoryIn the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with α-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 Pearson's hard and soft acid base theory.Facultad de Ciencias Exactas2014-01-14info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf285-294http://sedici.unlp.edu.ar/handle/10915/133530enginfo:eu-repo/semantics/altIdentifier/issn/1573-501xinfo:eu-repo/semantics/altIdentifier/issn/1381-1991info:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-013-9499-xinfo:eu-repo/semantics/altIdentifier/pmid/24420794info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:31:47Zoai:sedici.unlp.edu.ar:10915/133530Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:31:47.295SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv A serendipitous one-step conversion 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 one-step conversion 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 one-step conversion of 3H-1,2-dithiole-3-thione to (E)-3-(1-(alkylthio)alkylidene)-3H-1,2-dithiole: an experimental and theoretical study
Couto, Marcos
Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
title_short A serendipitous one-step conversion 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 one-step conversion 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 one-step conversion 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 one-step conversion 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 one-step conversion 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 Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
topic Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
dc.description.none.fl_txt_mv In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with α-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 Pearson's hard and soft acid base theory.
Facultad de Ciencias Exactas
description In the course of our studies on 3H-1,2-dithiole-3-thione synthesis, a serendipitous reactivity with α-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 Pearson's hard and soft acid base theory.
publishDate 2014
dc.date.none.fl_str_mv 2014-01-14
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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://sedici.unlp.edu.ar/handle/10915/133530
url http://sedici.unlp.edu.ar/handle/10915/133530
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1573-501x
info:eu-repo/semantics/altIdentifier/issn/1381-1991
info:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-013-9499-x
info:eu-repo/semantics/altIdentifier/pmid/24420794
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
285-294
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
_version_ 1844616197228724224
score 13.070432

Publicaciones similares