• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

C-Si bond formation and fluoro(2.2)cylophane synthesis by C-F bond activation

Research Project

Project/Area Number 12450356
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionOKAYAMA UNIVERSITY

Principal Investigator

UNEYAMA Kenji  School of Natural Science and Technology, Professor, 自然科学研究科, 教授 (00033150)

Co-Investigator(Kenkyū-buntansha) AMII Hideki  School of Natural Science and Technology, Research associate, 自然科学研究科, 助手 (00284084)
KATAGIRI Toshimasa  School of Natural Science and Technology, Associate Professor, 自然科学研究科, 助教授 (70202009)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥15,000,000 (Direct Cost: ¥15,000,000)
Fiscal Year 2002: ¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2001: ¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 2000: ¥7,500,000 (Direct Cost: ¥7,500,000)
Keywordsfluorination / cyclophane / fluorine / 絶縁膜 / フッ素系材料 / パラ シクロファン / フッ素化合物 / フルオロ化 / フルオロシクロファン / 絶縁体
Research Abstract

Fluorocyclophanes have been recognized as a promising monomer for thermally stable insulator polymer useful for large scale semiconductor manufacturing. In order to develop a practical synthetic method for the cyclophane, Mg-promoted C-F bond activtion has been extensively studied. And one of the protocol for the purpose has been found which consists of reaction of bistrifluoromethyl benzene wirh magnesium in the presence of trimethylsilane in DMF. The reaction provided the desired trimethylsilylated benzyl compound in 50-60% yields. Fluroride-catalyzed desilylated defluorination gave the desired cyclophane via quinodimethane in 53% yield. The present method will be competitive to the Dolbier method based on Zn-metal promoted dechlorinative preparation from the point of availability of bistrifluoromethylbenzene.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Jian Hao, Hironari Ohkura, Hideki Amii, Kenji Uneyama: "A Novel Intramolecular Defluorinative cyclization Approach to the Synthesis of Difluoromethylated Quinazolic Acid Derivatives"Chem.Commun.. 1883-1884 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Masayuki Mae, Hideki Amii, Kenji Uneyama: "First Synthesis of 3,3-difluoroserine and cysteine Derivatives via Mg(0)-promoted C-F Bond Cleavage of Trifluoromethylimines"Tetrahedron Lett. 41. 7893-7896 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hideki Amii, Takeshi Kobayashi, Kenji Uneyama: "A Practical and Highly Efficient Synthesis of α-(Trimethylsilyl)-α,α-difluoroacetates"Synthesis. 2001-2003 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Satoru Kobayashi, Youko Yamamoto, Hideki Amii, Kenji Uneyama: "Preparation and Thermal Behavior of 3,3,4,4-Trafluorocyclobutane-1,2-diols : A New Family of Cyclobutane-1,2-diols"Chem.Lett. 1366-1367 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hideki Amii, Takeshi Kobayashi, Hiroshi Terasawa, Kenji Uneyama: "Difluorinated Danishefsky's Dienes : a Vasatile C4-building Block for the Fluorinated 6-Membered Ring"Org.Lett. 3. 3103-3105 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hideki Amii, Yasushi Hatamoto, Motoharu Seo, Kenji Uneyama: "A New C-F Bond Cleavage route for the Synthesis of Octfluoro[2.2]paracyclophane (AF4)"J.Org.Chem. 66. 7216-7218 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "A Novel Intramolecular Defluorinative cyclization Approach to the Synthesis of Difluoromethylated Quinazolfc Acid Derivatives"Chem. Commun.. 1883-1884 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "First Synthesis of 3,3-difluoroserine and cysteine Derivatives via Mg(0)-promoted C-F Bond Cleavage of Trifluoromethylimines"Tetrahedron Lett.. 41. 7893-7896 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "A Practical and Highly Efficient Synthesis of α-(Trimethylsilyl)-α,α-difluoroacetates"Synthesis. 2001-2003 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "Preparation and Thermal Behavior of 3,3,4,4-Trafluorocyclobutane-1,2-diols : A New Family of Cyclobutane-1,2-diols"Chem. Lett.. 1366-1367 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "Efficient Synthesis of an Optically Pure β-Bromo-β,β difluoroalanine Derivative, a General Precursor for β,β-Difluoroamino Acids"Tetrahedron : Asymmetry. 12. 1303-1311 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "Difluorinated Danishefsky's Dienes : a Vasatile C4-building Block for the Fluorinated 6-Membered Ring"Org. Lett.. 3. 3103-3105 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "A New C-F Bond Cleavage route for the Synthesis of Octfluoro[2.2]para-cyclophane (AF4)"J. Org. Chem.. 66. 7216-7218 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "A facile Synthesis of Difluoromethylaziridines"Tetrahedron Lett.. 43. 2069-2072 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] "A New Sequential Defluorination Route to α-Fluoro-α,β-unsaturated Ketones from Trifluoromethyl Ketones"Tetrahedron Lett.. 43. 6099-6102 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Hata, T.Kobayashi, H.Amii, K.Oneyama, J.T.Welch: "A new sequential defluorination route to α-fluoro-α,β-unsaturated katones from trifluoromethil ketones"Tetrahedron Letters. 43. 6099-6102 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Uneyama, H.Amii: "A review of Mg metal-promoted C-F bond activation ; a reliable synthetic approach to difluorinated organic compounds"Journal of Fluorine Chemistry. 114. 127-131 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Amii, T.Kobayashi, H.Terasawa, K.Uneyama: "Diflucrirated Danishefskys Diene : A Versatile C_4 Building Black for the Fluorinated Six-membered Rings"Organic Letters. 3. 3103-3105 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Amii, Y.Hatamoto, M.Seo, K.Uneyama: "A New C-F Bond-Cleavage Reute for the Synthesis of Octafluoro[2.2] para cyclophane"Journal of Organic Chemistry. 66. 7216-7218 (2001)

    • Related Report
      2001 Annual Research Report

URL: 

Published: 2000-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi