One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent (Beilstein Journal of Organic Chemistry)

Abstract A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni’s reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C–N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments. Beilstein J. Org. Chem. 2017, 13, 2502–2508. doi:10.3762/bjoc.13.247