Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination.

• Furuta Satoru

  Research Laboratory of Resources Utilization, Tokyo Institute of Technology

• Kuroboshi Manabu

  Research Laboratory of Resources Utilization, Tokyo Institute of Technology

• Hiyama Tamejiro

  Research Laboratory of Resources Utilization, Tokyo Institute of Technology

書誌事項

タイトル別名

• Fluorination of Orthothioesters through

抄録

The oxidative desulfurization-fluorination of orthothioesters of type RCH₂C(SMe)₃ using n-Bu₄NH₂F₃ and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF₂SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF₂ via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)₃ or RCH(OAc)C(SMe)₃ were fluorinated to afford difluoro ketones RCOCF₂SMe or difluoro acetates RCH(OAc)CF₂SMe, respectively. The difluoro acetates were reduced to RCH(OAc)CF₂H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 71 (8), 1939-1951, 1998

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390282679099121920
• NII論文ID: 130004150184
• NII論文ID: 10008935634
• NII書誌ID: AA00580132
• DOI: 10.1246/bcsj.71.1939
• ISSN: 13480634
• ISSN: 00092673
• ISSN: http://id.crossref.org/issn/00092673
• NDL書誌ID: 4547498
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4547498
• Web Site: https://academic.oup.com/bcsj/article-pdf/71/8/1939/56195517/bcsj.71.1939.pdf
• 本文言語コード: en
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