Reaction of hexafluorothioacetone dimer with azoles. Practical synthesis of N-(hexafluoro-iso-propyl)azoles

• Reaction of 1,1,3,3-tetrakis(trifluoromethyl)dithietane with azoles.
• Practical synthesis of N-(hexafluoro-iso-propyl)azoles.
• Introduction of (CF3)2CH-group into nitrogen-containing heterocycles.

The reaction of azoles with 2,2,4,4-tetrakis-(trifluoromethyl)-1,3-dithietane led to the unexpected formation of N-(hexafluoro-isopropyl)azoles and sulfur, providing access to a group of compounds bearing a (CF3)2CH-group at nitrogen. Imidazole, pyrazole, 1,2,3- and 1,2,4-triazoles and benzo-derivatives of imidazole and triazole were found to undergo alkylation via reaction with 2,2,4,4-tetrakis-(trifluoromethyl)-1,3-dithietane, producing the corresponding derivatives in 54–83% yield.

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