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Updated: Feb 17, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni's reagent
Azim Ziyaei Halimehjani1, Martin Dračínský2, Petr Beier2
1Faculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh St., Tehran, Iran.
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.
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