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ペルフルオロエノラートの生成と合成的利用に関する研究

Research Project

Project/Area Number 62470079
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionTokyo Institute of Technology

Principal Investigator

NAKAI Takeshi  Faculty of Engineering, Tokyo Institute of Tcchnology, 工学部, 教授 (90016717)

Co-Investigator(Kenkyū-buntansha) MIKAMI Koichi  Faculty of Engineering, Tokyo Institute of Tcchnology, 工学部, 助教授 (10157448)
Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥5,700,000 (Direct Cost: ¥5,700,000)
Fiscal Year 1988: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1987: ¥3,600,000 (Direct Cost: ¥3,600,000)
KeywordsFluorine Chemistry / Perfluoro-enolate / Enolate / Aldol Reaction / Ambident Reactivity / Polyfluoro-enolate / ペルフルオロオレフィン / リチウムペルフルオロプロペノラート / 異常求電子反応性
Research Abstract

In contrast to the central position of enolate chemistry in synthetic organic chemistry, perfluorinated enolate (F-enolate) chemistry, despite its great potential, remains unexplored. In the present research project, we have successfully developed a facile and general method for selective generation of metal F-enolate such as CF_3C(OM)=CF_2 and R_fC(OM)=CFCF_3 (M=Li, Na, and K) from polyfluorinated alcohols (R_fCH(OH)R_f'). The "dehydrofluorinative" generation metod has been shown to exhibit a high level of regioselection and/or stereoselection in the F-enolate formation.
Furthermore the F-enolate thus generated have been demonstrated to exhibit a unique and wide spectrum of reactivity toward both electrophilic and nucleophilic reagents. Of particular interest is that the F-enolates show not only the normal enolate reactivities (O- and C-nucleophilicity) including the aldol reactivity, but also the "unusual" electrophlic reactivity toward organometallic reagents such as rli and RM_gX to generate the -alkylated F-enolates (polyfluorinated enolate) such as R@>D2f@>D2C(OM)=CF-Bu. Finally, the unique reactivities of such polyfluorinated enolate have been defined.

Report

(3 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Cheng-Ping Qian: Tetrahedron Letters. 29. 4119-4122 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Takeshi Nakai: Abstract of 12th International Symposium on Fluorine Chemistry. 302 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 中井武: 化学素材研究開発振興財団研究報告. 3. 31-33 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 銭承平: 日本化学会第56回春季年会講演予稿集. II. 1247 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 銭承平: 日本化学会第56回春季年会講演予稿集. II. 1247 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 銭承平: 日本化学会第58回春季年会講演予稿集. II. (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Cheng-Ping Qian: "Perfluoro-enolate Chemistry: Facile Generation and Unique Reactivities of Metal F-1-Propen-2-Olates" Tetrahedron Letters. 29. 4119-4122 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Takeshi Nakai: "Perfluoro-enolate Chemistry: Facile Generation and Unique Reactivities of Metal F-Propen-2-Olate and Its Homologues" Abstract of 12th International Symposium of Fluorine Chemistry. 302 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Takeshi Nakai: "Exploration of Perfluoro-enolate Chemistry and Its Synthetic Applications" Reseach Report of Foundation for Development of Chemical Materials. 3. 31-33 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Cheng-Ping Qian: "Perfluoro-enolate Chemistry (#3). Regioselective Generation of beta-CF_3-Substituted F-enolates and Their Abstract of The 56th Annual" Meeting of Reactivities Chemical Society of Japan. II. 1247 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Cheng-Ping Qian: "Perfluoro-enolate Chemistry (#4). Unique Reactivity of Polyfluorinated Enolates Generated from Perfluoro-enolates" Abstract of The 56th Annual Meeting of Chemical Society of Japan. II. 1247 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Cheng-Ping,Qian: Tetrahedron Letters. 29. 4119-4122 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Takeshi,Nakai: Abstract of 12th International Symposium on Fluorine Chemistry. 302 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 中井武: 化学素材研究開発振興財団研究報告. 3. 31-33 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 銭承平: 日本化学会第56回春季年会講演予稿集. 11. 1247 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 銭承平: 日本化学会第56回春季年会講演予稿集. 11. 1247 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 銭承平: 日本化学会第58回春季年会講演予稿集. 11. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 銭承平: 日本化学会第54春期年会講演予稿集. II. 1355 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] 銭承平: 日本化学会第54春季年会講演予稿集. II. 1355 (1987)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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