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A Facile Preparation of Arenes having Fluorine-Containing Functional Groups using Fluorine-Containing Strong Acids.

Research Project

Project/Area Number 02650596
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionHokkaido University

Principal Investigator

YONEDA Norihiko  Hokkaido Univ., Fac. of Eng., Professor, 工学部, 教授 (50001219)

Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1991: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1990: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsFluorination / Diazotization / Dediazoniation / Diazonium Salt / HF-Base / Aryl Triflate / Fluorophenol / 含フッ素化合物 / トリフラ-ト / トリフルオロメタンスルホン酸 / フッ化水素ー塩基溶液 / ジアゾ化・脱ジアゾフッ素化反応 / Pーフルオロフェノ-ル / ベンゾキノン / キノンジアザイド
Research Abstract

Aromatic (including heterocyclic) compounds having fluorine-containing functional groups (ArX : X=F, OSO_2CF_3, OSO_2F, OCOCF_3) have been prepared in good yields by the diazotization of the corresponding aminoarenes (ArNH_2) and the thermal or photochemical decomposition in situ in fluorine containing strong acids (HX) with or without bases, or dediazoniation of arenediazonium tetrafluoroborate salts (ArN_2BF_4) in HX-(Base).
Novel arenediazonium of triflates (ArN_2BF_4) have been prepared in good yields by nonaqueous state diazotization of ArNH_2 in EtOH with isoamyl nitrate in CF_3SO_3H. Decomposition of ArN_2OTr will be also described to afford the corresponding ArOSO_2CF_3.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] T.Fukuhara,N.Yneda,K.Takamura,and A.Suzuki,: "Preparation of p-Fluourphenols from p-Aminophenols:Diazotization and Fluourodediazoniation in Pyridine-HF" J.Fluorine Chem.51. 299-304 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] N.Yoneda,T.Fukuhara,T.Mizokami,and A. Suzuki: "A Facile Preparation of Aryl Trifrates:Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethaneslufonic Acid" Chem.Lett.459-460 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] N.Yoneda,: "The Combination of Hydrogen Fluoride with Organic Bases as Fluorination Agents" Tetrahedron. 47. 5329-5365 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] T. Fukuhara, N. Yoneda, K. Takamura, and A. Suzuki: "Preparation of p-Fluorophenols from p-Aminophenols : Diazotization and Fluorodediazoniation in Pyridine-HF" J. Fluorine Chem.51. 299 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] N. Yoneda, T. Fukuhara, T. Mizokami, and A. Suzuki: "A Facile Preparation of Aryl Trifrates : Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethaneslufonic Acid" Chem. Lett.459. (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] N. Yoneda: "The Combination of Hydrogen Fluoride with Organic Bases as Fluorination Agents" Tetrahedron. 47. 5329 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] T.Fukuhara,N.Yoneda,K.Takamura,and A.Suzuki,: "Preparation of pーFluorophenols from pーAminophenols:Diazotization and Fluorodediazoniation in PyridineーHF" J.Fluorine Chem.51. 299-304 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] N.Yoneda,T.Fukuhara,T.Mizokami,and A.Suzuki,: "A Facile Prepation of Aryl Trifrates:Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethaneslufonic Acid" Chem.Lett.459-460 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] N.Yoneda,: "The Combination of Hydrogen Fluoride with Organic Bases as Fluorination Agents" Tetrahedron. 47. 5329-5365 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Fukuhara: "Preparation of pーFluorophenols from pーAminophenols:Diazotization and Fluorodediazoniation in PyridineーHF" J.Fluorine Chem.

    • Related Report
      1990 Annual Research Report
  • [Publications] N.Yoneda: "A Facile Preparation of Aryl Trifrates.Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethanslufonic Acid" Chem.Lett.459-460 (1991)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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