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One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni's reagent.

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.

SUBMITTER: Halimehjani AZ

PROVIDER: S-EPMC5704766 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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One-pot three-component route for the synthesis of <i>S</i>-trifluoromethyl dithiocarbamates using Togni's reagent.

Halimehjani Azim Ziyaei AZ Dračínský Martin M Beier Petr P

Beilstein journal of organic chemistry 20171124

A one-pot three-component route for the synthesis of <i>S</i>-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, p ...[more]

PMID: 29234477

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