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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. 2014

Marcos Couto, and Mauricio Cabrera, and Gustavo A Echeverría, and Oscar E Piro, and Mercedes González, and Hugo Cerecetto
Grupo de Química Medicinal, Facultad de Química-Facultad de Ciencias, Universidad de la República, Iguá 4225, Montevideo, 11400, Uruguay.

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.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D011789 Quantum Theory The theory that the radiation and absorption of energy take place in definite quantities called quanta (E) which vary in size and are defined by the equation E Quantum Theories,Theories, Quantum,Theory, Quantum
D013871 Thiones Sulfur-containing compounds also known as thioketones of general formula R2C Thioketone,Thione,Thioketones
D013876 Thiophenes A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur. Thiophene
D014050 Toluene A widely used industrial solvent.
D018890 Chemoprevention The use of chemical compounds to prevent the development of a specific disease. Chemoprophylaxis

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