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

Kiyoshi Kanie, Yoichiro Tanaka, Kazundo Suzuki, Manabu Kuroboshi, Tamejiro Hiyama

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58 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)471-484
Number of pages14
JournalBulletin of the Chemical Society of Japan
Volume73
Issue number2
DOIs
Publication statusPublished - Feb 1 2000

ASJC Scopus subject areas

  • Chemistry(all)

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