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

Authors :
Couto, Marcos
Cabrera, Mauricio
Echeverría, Gustavo
Piro, Oscar
González, Mercedes
Cerecetto, Hugo
Source :
Molecular Diversity; May2014, Vol. 18 Issue 2, p285-294, 10p
Publication Year :
2014

Abstract

In the course of our studies on 3 $$H$$ -1,2-dithiole-3-thione synthesis, a serendipitous reactivity with $$\alpha $$ -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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
13811991
Volume :
18
Issue :
2
Database :
Complementary Index
Journal :
Molecular Diversity
Publication Type :
Academic Journal
Accession number :
95344612
Full Text :
https://doi.org/10.1007/s11030-013-9499-x