Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers

Manabu Kuroboshi, Kazundo Suzuki, Tamejiro Hiyama

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide.

Original languageEnglish
Pages (from-to)4173-4176
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number29
DOIs
Publication statusPublished - Jul 14 1992
Externally publishedYes

Fingerprint

Bromosuccinimide
Methyl Ethers
Fluorination
Ethers
Halogenation
Desulfurization
1,3-dibromo-5,5-dimethylhydantoin

Keywords

  • oxidative desulfurization-fluorination
  • trifluoromethyl ethers
  • xanthates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers. / Kuroboshi, Manabu; Suzuki, Kazundo; Hiyama, Tamejiro.

In: Tetrahedron Letters, Vol. 33, No. 29, 14.07.1992, p. 4173-4176.

Research output: Contribution to journalArticle

@article{c6e9abefd6fc42b29e814797cf364f9e,
title = "Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers",
abstract = "Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide.",
keywords = "oxidative desulfurization-fluorination, trifluoromethyl ethers, xanthates",
author = "Manabu Kuroboshi and Kazundo Suzuki and Tamejiro Hiyama",
year = "1992",
month = "7",
day = "14",
doi = "10.1016/S0040-4039(00)74681-8",
language = "English",
volume = "33",
pages = "4173--4176",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "29",

}

TY - JOUR

T1 - Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers

AU - Kuroboshi, Manabu

AU - Suzuki, Kazundo

AU - Hiyama, Tamejiro

PY - 1992/7/14

Y1 - 1992/7/14

N2 - Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide.

AB - Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide.

KW - oxidative desulfurization-fluorination

KW - trifluoromethyl ethers

KW - xanthates

UR - http://www.scopus.com/inward/record.url?scp=0026719708&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026719708&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)74681-8

DO - 10.1016/S0040-4039(00)74681-8

M3 - Article

AN - SCOPUS:0026719708

VL - 33

SP - 4173

EP - 4176

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -