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Organic Syntheses Utilizing Trimethylsilyldiazomethane

Research Project

Project/Area Number 63571001
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagoya City University

Principal Investigator

AOYAMA Toyohiko  Nagoya City University, Faculty of Pharmaceutical Sciences, Lecturer, 薬学部, 講師 (80080191)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordstrimethylsilyldiazomethane / lithium trimethylsilyldiazomethane / alpha-trimethylsilyldiazoalkane / (E)-vinylsilane / (Z)-vinylsilane / 1, 2, 3-triazole / olefin / quinone / ハロゲン化アルキル / α-トリメチルシリルジアゾアルカン / (Z)-ビニルシラン / 1,3-双極子環化付加反応 / インダゾ-ル / ケテンイミン / 1.2.3ートリアゾール / シリルシクロプロパン
Research Abstract

Synthetic utilizations of trimethylsilyldiazomethane (TMSCHN_2), as a stable and safe substitute for hazardous diazomethane, were investigated as follows: 1. The cuprous chloride-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes gives (E)-1-trimethylsilyl-1-alkenes in high yields. 2. Lithium trimethylsilyldiazomethane smoothly reacts with ketenimines to give 1,2,3-triazoles in good yields. 3. Most of the reactions of TMSCHN_2 with various olefins in the presence or absence of metal salt catalysts give silylcyclopropanes. 4. The rhodium(II) pivalate-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes stereoselectively affords (Z)-1-trimethylsilyl-1-alkenes,in,good yields. 5. Reaction of TMSCHN_2 with various quinones affords indazoles, silylcyclopropanes, 2-substituted 3-trimethylsilylmethylml,4-quinones, and trimethylsilylmethylenedioxy derivatives,depending upon substrates.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] Toyohiko Aoyama: "Trimethylsilyldiazomethane:A Convenient Reagent for the Preparation of(E)-1-Trimethylsilyl-l-alkenes" Tetrahedron Lett.29. 6295-6296 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Lithium Trimethylsilyldiazomethane:A Useful Reagent for the Preparation of 1,2,3-Triazoles from Ketenimines" Heterocycles. 28. 133-136 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Olefins" Chem.Pharm.Bull.37. 253-256 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Trimethylsilyldiazomethane:A Useful Reagent for the Preparation of(Z)-1-Trimethylsilyl-1-alkenes" Chem.Pharm.Bull.37. 2261-2262 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takayuki Shioiri: "Trimethylsilyldiazomethane" Org.Syntheses. 68. 1-7 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Quinones" Heterocycles. 30. 375-379 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Trimethylsilyldiazomethane: A Convenient Reagent for the Preparation of (E)-1-Trimethylsilyl-1-alkenes" Tetrahedron Lett. 29-48, 6295-6296 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Lithium Trimethylsilyldiazomethane: A Useful Reagent for the Preparation of 1, 2, 3-Triazoles from Ketenimines" Heterocycles 28-1, 133-136 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Olefins" Chem. Pharm. Bull. 37-1, 253-256 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Trimethylsilyldiazomethane: A Useful Reagent for the Preparation of (Z)-1-Trimethylsilyl-1-alkenes" Chem. Pharm. Bull. 37-8, 2261-2262 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takayuki Shioiri: "Trimethylsilyldiazomethane" Org. Syntheses 68, 1-7 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Quinones" Heterocycles 30-1, 375-379 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toyohiko Aoyama: "Trimethylsilyldiazomethane: A Useful Reagent for the Preparation of(Z)-l-Trimethylsilyl-l-alkenes" Chem.Pharm.Bull.37. 2261-2262 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takayuki Shioiri: "Trimethylsilyldiazometahne" Org.Syntheses. 68. 1-7 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Toyohikol Aoyama: "Reaction of Trimethylsilyldiazomethane with Quinones" Heterocycles. 30. 375-379 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Toyohiko Aoyama: Tetrahedron Lett.29. 6295-6296 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Toyohiko Aoyama: Heterocycles. 28. 133-146 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Toyohiko Aoyama: Chem.Pharm.Bull.37. 253-256 (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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