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Syntheses and Properties of Allene・Cumulene Compounds Connecting with Non-benzenoid Aromatics

Research Project

Project/Area Number 61470022
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionUtsunomiya University

Principal Investigator

TODA Takashi  Utsunomiya University, Faculty of Engineering, 工学部, 教授 (20004278)

Co-Investigator(Kenkyū-buntansha) YOSHIDA Masaaki  Utsunomiya University, Faculty of Engineering, 工学部, 助手 (90114173)
MINABE Masahiro  Utsunomiya University, Faculty of Engineering, 工学部, 助教授 (40007993)
Project Period (FY) 1986 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥7,000,000 (Direct Cost: ¥7,000,000)
Fiscal Year 1988: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥5,600,000 (Direct Cost: ¥5,600,000)
KeywordsCycloheptatrienylidene-ethenes / Cyclopentadienylidene-ethenes / Cycloheptatrienylidenecyclopentadienylidene-ethenes / Aminocinnamhydrazides / Styrilformazans / 縮合多環芳香族化合物 / シクロヘプタシクロペンタジエニリデンエテン類 / テトラフェニルシクロペンテニルエテン類 / 環状付加反応 / アセチルアミノピレン類 / ベンゾ〔a〕インデノ〔1、2、3-cd〕アズレン類 / テトラアリールサイクロン誘導体 / シクロヘプタトリエニリデンシクロペンチジエニリデンエチレン誘通体 / アリールフルオニリデン誘導体 / アリールプロパジェン誘導体 / 熱二量化反応 / シクロプロペニリデンエテン類 / シクロペンタジェニリデンエテン類 / シクロヘプタトリエニリデンシクロペンタジェニリデンエテン類 / 【S_2】よりの発光 / ピラゾロン誘導体の生成
Research Abstract

The purpose of our project is to synthesize cumulated compounds which possess conjugate system with non-benzenoid aromatics such as cycloheptatrienylidene, cyclopentadienylidene or cyclopropenylidenes, and to investigate chemical and physical properties of those novel conjugate compounds.
For this, arylcycloheptatrienylidene-ethenes were synthesized and it was found that those compounds readily gave three different kinds of dimer which properties were also investigated.
Some cyclopentadienylideneethenes have been reported, but their thermal unstability did not allow detailed studies. We found that substitution of hydrogen atom at the C-1 position by bromine atom makes those system stable and some cyclopentadienylidene-ethenes were obtained. Several physical properties and thermal dimerization reactions of the cyclopentadienylidenes including some arylallene derivatives were investigated. As the results, the dimerization mechanisms are established.
Syntheses of cyclopropenylidene derivatives have not been succeeded yet. Further attempts will be made in feature. Additional research has been done about reactions of diphenylcyclopropenone with hydrazines and multiple reactivities of this system has been explored to give pyrazole derivatives via cinnamhydrazides and also styrilformazan derivatives.
Several pyrene derivatives and benz[a]indeno[1,2,3-cd]azulene derivatives were synthesized and their chemical properties were investigated as new materials for complex formation and for arylallene derivatives' syntheses.

Report

(4 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • 1986 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] T.Toda,;N.Shimazaki,;T.Mukai: Chemistry Letters. 171-174 (1979)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Toda,;N.Shimazaki,;T.Mukai,;C.Kabuto: Tetrahedron Letters. 21. 4001-4004 (1980)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] A.Tajiri,;M.Hatano,;T.Toda,;N.Shimazaki,;T.Mukai: Chemistry and Physics Letters. 81. 251-255 (1981)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Toda,;N.Shimazaki,;H.Hotta,;T.Hatakeyama,;T.Mukai: Chemistry Letters. 523-526 (1983)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Toda,;M.Yoshida,;T.Katayama,;M.Minabe: Heterocycles. 25. 79-82 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Toda,;N.Shimazaki,;T.Mukai: Angew.Chem.Int.Ed.Engl.26. 335-336 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T. Toda; N. Shimazaki; T. Mukai: "1-Cycloheptatrienylidene-2-phenylethylene and its Intriguing Dimerization Reactions" Chemistry Letters. 171-174 (1979)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T. Toda; N. Shimazaki; T, Mukai; C. Kabuto: "Synthesis and Physical Properties of 6,12-Diarylazuleno[1,2-b]azulenes" Tetrahedron Letters. 21. 4001-4004 (1980)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] A. Tajiri; M. Hatano; T. Toda; N. Shimazaki; T. Mukai: "Magnetic Circular Dichroism of Azuleno[1,2-b]azulene Derivatives" Chemical Physics Letters. 81. 251-255 (1981)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T. Toda; N. Shimazaki; H. Hotta; T. Hatakeyama; T. Mukai: "dual Reactivity of Cycloheptatriene and Norcaradiene Valence Isomerization System" Chemistry Letters. 523-526 (1983)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T. Toda; M. Yoshida; T. Katayama; M. Minabe: "Reactions of Diphenylcyclopropanone with Hydrazine Derivatives: Formation of Pyrazolone Derivatives via 3-Aminocinnamohydrazide" Heterocycles. 25. 79-82 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] M.Minabe;M.Yoshida;S.Saito;K.Tobita;T.Toda: Bull.Chem.Soc.Jpn.61. 2067-2070 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Minabe;H.Mochizuki;M.Yoshida;T.Toda: Bull.Chem.Soc.Jpn.62. 68-72 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Toda;N.Shimazaki;T.Mukai: Angew.Chem.Int.Ed.Engl. 26. 335-336 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] M.Minabe;M.Yoshida;S.Saito;K.Tobita;T.Toda: Bull.Chem.Soc.Japan. 61. NO6 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Toda;M.Yoshida;T.Katayama;M.Minade: Heterocycles. 25. 79-82 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] T.Toda;N.Shimazaki;T.Mukai: Angew.Chem.99. (1987)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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