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Conversion of perfluorotrisubstituted olefin to functional

Research Project

Project/Area Number 02555178
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

IKEDA Isao  Osaka University, Faculty of Engineering, Professor, 工学部, 教授 (70029049)

Co-Investigator(Kenkyū-buntansha) NEMOTO Fujito  Neos Co., Central Research Institute, Manager, 中央研究所, 所長
KUROSAWA Hideo  Osaka University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (40029343)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1991: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1990: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywordsperfluoro-trisubstituted Olefin / perfluoro-2-methyl-2-pentene / Fluorine-containing Heterocyclic Compound / 4-fluorinated Pyrimidine / perfluoroalkyl-substituted Pyrimidine / (perfluoro-tertiaryalkyl) Methyloxylation / 表面改質 / ペルフルオロ-2-メチル-2-ペンテン / 4-フッ化ピリミジン / 二座求核体
Research Abstract

Since the fluorine-containing compounds are valuable as organic materials, studies on the synthesis of novel compounds, their utilization, and their properties are becoming more active. One of the most important uses of those compounds are concering the surface improvement of solid and liquid, because of the extreme low surface trnsion or surface energy of perfluoroalkyl-containig compounds.
In the present study, one isomer of perfluoropropyrene dimers, perfluoro-2-methyl-2-pentene, which is industrially produced but is stiff not valuable from the view point of utilization is focussed to the synthesis of fluorine-containing heterocyclic compounds and to the utilization to surface improvement.
As the results, it is clarified that 6-membered heterocyclic compounds, pyrimidines with various substituent at 2-position were obtained in good yields. It is also recognized that these compounds showed the peculiar reactivity. In spite of the aromatic compounds, their fluorine atom substituted at 4 … More -position can be replaced by various nucleophile by the influence of vivo perfluoroalkyl substituents on the aromatic ring. When perfluoroalkyl-containing compounds are utilized as surface improve, a certain spacer are usually introduced between hydrophilic and lipophilic moieties, otherwise those surface improve without such spacer ar-e difficult to exhibit their inherently excelent properties due to the rigidity of perfluoroalkyl group. In the present study, developed is the method to link the rigid tertiary perfluoroalkyl moiety and the chemically or physically active group, which can be easily derivatized to hydrophilic moiety, with the flexible oxymethylene spacer. Tbus, in dimethylformamide, perfluoro-2-methyl-2-pentene reacted with various chloromethyl ethers in the presence of potassium fluoride to afford (tertiary-perfluoroalkyl) methyloxy compounds. Industrially important is that this active group can consist of alkyl, allyl, aryl, aralkyl, haloalkyl, or ether group, and that these compounds can be easily derived to surface improver. Less

Report

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

    (8 results)

All Other

All Publications (8 results)

  • [Publications] 池田 功: "Synthesis of 2ーsubstitutedー4ーfluoroー5,6ーdiperufluoroーalkylpyrimidines and their reactivity" Journal of Fluorine Chemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 池田 功: "Perfluoroalkylation of chloromethyl ethers using perfluoroー2ーmethylー2ーpentene with potassium fluorideーDMF" Journal of Fluorine Chemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao IKEDA and Hideo KUROSAWA: "Synthesis of 2-substituted-4-fluoro-5, 6-diperufluoroalkylpyrimidines and their reactivity" Journal of Fluorine Chemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao IKEDA and Hideo KUROSAWA: "Perfluoroalkylation of chloromethyl ethers using perfluoro-2-methyl-2-pentene with potassium fluoride-dimethylformamide" Journal of Fluorine Chemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 池田 功: "Synthesis of 2-substituted-4-fluoro-5,6-diperufluoroalky1-pyrimidines and their reactivity" Journal of Fluorine Chemistry.

    • Related Report
      1991 Annual Research Report
  • [Publications] 池田 功: "Perfluoroalkylation of chloromethyl ethers using perfluoro-2-methyl-2-pentene with potassium fluoride-DMF" Journal of Fluorine Chemistry.

    • Related Report
      1991 Annual Research Report
  • [Publications] 池田 功,黒沢 英夫: "ペルフルオロー2ーメチルー2ーペンテンとアミジン類の反応による4ーフッ化ピリミジン類の合成と生成ピリミジンの求電子反応性" 有機化学雑誌(アメリカ化学会).

    • Related Report
      1990 Annual Research Report
  • [Publications] 池田 功,黒沢 英夫: "ペルフルオロー2ーメチルー2ーペンテンと一置換ヒドラジンの反応によるピラゾ-ル類の合成と生成ピラゾ-ルの反応性" 有機化学雑誌(アメリカ化学会).

    • Related Report
      1990 Annual Research Report

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

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