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

MARCOS COUTO; MAURICIO CABRERA; GUSTAVO A. ECHEVERRÍA; OSCAR E. PIRO; MERCEDES GONZALEZ; HUGO CERECETTO

MOLECULAR DIVERSITY

SPRINGER

Lugar: Berlin; Año: 2014 vol. 18 p. 285 - 294

1381-1991

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.