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

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

doi:10.1246/bcsj.73.471

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

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

Research output: Contribution to journal › Article › peer-review

36 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 language	English
Pages (from-to)	471-484
Number of pages	14
Journal	Bulletin of the Chemical Society of Japan
Volume	73
Issue number	2
DOIs	https://doi.org/10.1246/bcsj.73.471
Publication status	Published - Feb 2000

ASJC Scopus subject areas

Chemistry(all)

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title = "A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates",

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).",

author = "Kiyoshi Kanie and Yoichiro Tanaka and Kazundo Suzuki and Manabu Kuroboshi and Tamejiro Hiyama",

year = "2000",

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doi = "10.1246/bcsj.73.471",

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T1 - A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates

AU - Kanie, Kiyoshi

AU - Tanaka, Yoichiro

AU - Suzuki, Kazundo

AU - Kuroboshi, Manabu

AU - Hiyama, Tamejiro

PY - 2000/2

Y1 - 2000/2

N2 - 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).

AB - 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).

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DO - 10.1246/bcsj.73.471

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JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

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

Abstract

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