A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates

Article abstract of DOI:10.1246/bcsj.73.471

Trifluoromethyl ethers R-OCF₃ are easily synthesized from the corresponding dithiocarbonates R-OCS₂Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS₂Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N- bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF₃ (R = secondary).