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Development of New Reactions Using Charge Transfer Complex Based on New Concept

Research Project

Project/Area Number 11650879
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionFaculty of Science and Engineering, Kinki University

Principal Investigator

MATSUBARA Yoshio  Faculty of Science and Engineering, Kinki University, Professor, 理工学部, 教授 (80088450)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2000: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1999: ¥1,800,000 (Direct Cost: ¥1,800,000)
KeywordsCharge transfer complex / Phenylhydrazones-TCNE system / N,N-dimethylanilin / Tetrahalomethane system / Imine metathesis / Novel reaction / Producing 4,4'-methylenebis (N,N-dimetylaniline) / π-ドナー / π-アクセプター / σ-アクセプター / ヒドラゾン類 / TCNE / ジメチルアニリン / ハロメタン
Research Abstract

This study was investigated on the development of new reactions using charge transfer complex such as π-donor - π-acceptor system and π-donor - σ-acceptor system based on new concept as formation of radical ion pair dyad in specific solvation.
The results were noticeable such as showing below.
1) New imine metathesis obtaied olefin and hetero atom was found by the reaction of aromatic hydrazones (π-donor) with tetracyanoethylene (π-acceptor) in asetonitrile as specific solvent.
2) Novel reaction producing 4,4'-methylenebis(N,N-dimetylaniline) (major) 4,4', 4"-metylidyne-tris(N,N-dimethylaniline) (minor) and trace amount of N-[4[bis[4-(dimethylamino)-phenyl]methylene]-2,5-cyclohexadien-1-ylidene]-N- methylmethanaminum bromide was found by the reaction of N,N-dimetylanilines with tetrahalomethanes such as tetrabromomethane and tetrachlolomethane in acetonitrile. The reaction is cosidered to be initiated by the electron transfer from N,N-dimethylaniline (π-donor) to tetrahalomethane (σ-acceptor).

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] Y.Matsubara,T.Matsuda,Y.Yamaguchi: "Novel Reaction of Dimetylanilines with CBr_4 producing 4,4'-Metylenebis (N,N-dimetylanilines)"J.Chem.Soc, Chem.Commum,. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Matsubara,T.Matsuda,Z.Yoshida: "Electrochemical Transformation of 4-Cyanocinnolines into 4(1H)-Cinnolones"Tetrahedron Lett.,. 41. 7901-7904 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Matsubara, T.Matsuda, Y.Yamaguchi: "Novel Reaction of Dimetylanilines with CBr_4 producing 4,4'-Metylenebis(N,N-dimetylanilines)"J.Chem.Soc, Chem.Commum. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Matsubara, T.Matsuda, Z.Yoshida: "Electrochemical Transformation of 4-Cyanocinnolines into 4(1H)-Cinnolones"Tetrahedron Lett.. 41. 7901-7904 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 松原凱男: "Electrochemical Transformation of 4-Cyanocinnolines into 4(1H)-Cinnolones"Tetrahedron Lett.. 41. 7901-7904 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 松原凱男: "Novel Reaction of Dimetylanilines with CBr_4 producing 4,4'-Metylenebis (N,N-dimetylanilines)"発表予定.

    • Related Report
      2000 Annual Research Report
  • [Publications] 松原凱男: "Imine Metathesis by the Reaction of Aromatic Hydrazones with Tetracyanoethylene"発表予定.

    • Related Report
      2000 Annual Research Report
  • [Publications] 松原凱男: "Echochemicaly Ideal Reaction Producting a New Class of Merocyanines"発表予定.

    • Related Report
      2000 Annual Research Report
  • [Publications] 松原凱男: "Remarkably Different Behavior of 4-Cyano-3-phenylcinnoline Toward Chemical and Electrochemical Reductions"Tetrahedron Lett.. (in press).

    • Related Report
      1999 Annual Research Report
  • [Publications] 松原凱男: "Reaction of Aromatic Hydrazones with Tetracyano-ethylene Leading to the Formation of Cyanocinnoline"発表予定.

    • Related Report
      1999 Annual Research Report
  • [Publications] 松原凱男: "Echochemicaly Ideal Reaction production a New Class of Merocyanines"発表予定.

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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