Cantillo David, Avalos Martín, Babiano Reyes, Cintas Pedro, Jiménez José L, Light Mark E, Palacios Juan C
Departamento de Química Orgánica e Inorgánica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain.
Org Lett. 2008 Mar 20;10(6):1079-82. doi: 10.1021/ol702929k. Epub 2008 Feb 16.
An unusual thionation strategy of mesoionic compounds with aryl isothiocyanates enables a facile synthesis of 1,3-thiazolium-4-thiolate systems. The mechanistic pathway of such a transformation most likely involves a stepwise 1,3-dipolar cycloaddition, which is supported by theoretical calculations performed with a two-layer hybrid method (B3LYP/6-31G(d):PM3).
