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

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 resul...

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Detalles Bibliográficos
Autores principales: Couto, Marcos, Cabrera, Mauricio, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, González, Mercedes, Cerecetto, Hugo
Formato: Articulo
Lenguaje:Inglés
Publicado: 2014
Materias:
Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/133530
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-133530
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
spellingShingle Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
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
topic_facet Química
3H-1,2-Dithiole-3-thione
(E)-3-Alkylidene3H-1,2-dithiole
DFT calculations
HSAB theory
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.
format Articulo
Articulo
author Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
author_facet Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
González, Mercedes
Cerecetto, Hugo
author_sort Couto, Marcos
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
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 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
publishDate 2014
url http://sedici.unlp.edu.ar/handle/10915/133530
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