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Interaction between the Cation Radicals and Weak-Nucleophilic Reagent in Photochemical Electron Transfer Systems.

Research Project

Project/Area Number 02640400
Research Category

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

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

Principal Investigator

YASUDA Masahide  Miyazaki University, Faculty of Engineering Associate Professor, 工学部, 助教授 (00174516)

Co-Investigator(Kenkyū-buntansha) TANABE Kimiko  Miyazaki University Faculty of Engineering Research Associate, 工学部, 助手 (00179805)
YAMASHITA Toshiaki  Miyakonojo National College of Technology, Research Associate, 助手 (80191287)
SHIMA Kensuke  Miyazaki University, Faculty of Engineering Professor, 工学部, 教授 (20029862)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsPhotochemical Electron Transfer / Photooxygenation / Photoamination / Photophosphonation / Cyanomethylation / 芳香族炭化水素 / スチルベン類 / 求核付加反応 / 1.1ージフェニルアルケン
Research Abstract

The interaction between the cation radicals generated by the photochemical electron transfer and various nucleophiles has been investigated.
(1)An Interaction with Acetate Anion. The photooxygenation of naphthalene derivatives in the presence of acetate anion gave pothalic acids whereas the photooxygenation in the absence of the salts gave naphthoquinone derivatives. Thus the acetate ion accelerate the reaction of the cation radicals with oxygen molecule.
(2)An Interaction with Amines. Regiochemistry on photoamination via the reaction of the cation radical with amines has been investigated for a dozen 1, 2-arylphenylethenes. A regioselective photoamination occurred in the stilbenes having the methoxy group at para position on aryl group. The amine added to 9-alkoxyphenanthrene mainly in trans manner to give cis-9-amino-10-alkoxy-9, 10-dihydrophenanthrene.
(3)An Interaction with Trialkylphosphites. The preparation of arene phosphonates was performed by the reaction of the cation radicals of phenanthrene or naphthalene with trialkyl phosphites.
(4)An Interaction with Acetonitrile. Cyanomethylation of 1, 1-diphenylalkenes was performed by the photoreaction in the presence of p-dicyanobenzene and t-butylamine in acetonitrile.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Toshiaki Yamashita: "Unusual Effects of Acetate Ion on Photosensitized Oxygenation of Naphthalene Derivatives via Electron Transfer" Chem.Lett.1487-1490 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Amination of Electron-Rich Substrates via Photoinduced Electron Transfer.Mechanism and Synthetic Application" Reviews on Heteroatom Chemistry. 4. 27-46 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Stereochemical studies on the Amination of Arenes with Ammonia and Alkylamines via Photochemical Electron Transfer" J.Chem.Soc.Perkin Trans.2,. 305-310 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Regiochemistry on Photoamination of Stilbene Derivatives with Ammonia via Electron Transfer" J.Org.Chem.57. 1351-1354 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Application of Photoamination of Synthesis of Benzylioquinoline,Aporphines,and Isopavines" Heterocycles.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Kensuke Shima: "Ring-Splitting Reaction of 2,2-Diarylthietane by Electron TRansfer Photosensitization of 9,10-Dicyanoanthracene" Bull.Chem.Soc.Jpn.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Unusual Effects of Acetate Ion on Photosensitized Oxygenation of Naphthalene Derivatives via Electron Transfer" Chem. Lett.1487 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Amination of Electron-Rich Substrates via Photoinduced Electron Transfer. Mechanism and Synthetic Application" Reviews on Heteroatom Chemistry. 4. 27 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Stereochemical Studies on the Amination of Arenes with Ammonia and Alkylamines via Photochemical Electron Transfer" J. Chem. Soc. Perkin Trans.2. 305 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Regiochemistry on Photoamination of Stilbenes Derivatives with Ammonia via Electron Transfer" J. Org. Chem.57-5. 1352 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Application of Photoamination to Synthesis of Benzylisoquinolines, Aporphines, and Isopavines" Heterocycles.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Kensuke Shima: "Ring-Splitting Reaction of 2, 2-Diarylthietane by Electron Transfer Photosensitization of 9, 10-Dicyanoanthracene" Bull. Chem. Soc. Jpn.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Toshiaki Yamashita: "Unusual Effects of Acetate Ion on Photosensitized Oxygenation of Naphtalene Derivatives via Electron Transfer" Chem.Lett.1487-1490 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahide Yasuda: "Amination of ElectronーRich Substrates via Photoinduced Electron Transfer.Mechanism and Synthetic Application" Reviews on Heteroatom Chemistry. 4. 27-46 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahide Yasuda: "Stereochemical Studies on the Amination of Arenes with Ammonia and Alkylamines via Photochemical Electron Transfer" J.Chem.Soc.Perkin Trans.2,. 305-310 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahide Yasuda: "Regiochemistry on Photoamination of Stilbene Derivatives with Ammonia via Electron Transfer" J.Org.Chem.57. 1351-1354 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahide Yasuda: "Application of Photoamination to Synthesis of Benzylisoquinoline ,Aporphines,and Isopavines" Heterocycles.

    • Related Report
      1991 Annual Research Report
  • [Publications] Kensuke Shima: "RingーSplitting Reaction of 2,2ーDiarylthietane by Electron Transfer Photosensitization of 9,10ーoicyanoanthracene" Bull.Chem.Soc Jpn.

    • Related Report
      1991 Annual Research Report
  • [Publications] Toshiaki Yamashita: "Photoーinduced Nucleophilic Addition of Ammonia and AlkylーAmines to ArylーSubstituted Alkenes in the Presence of pーDicyanobenzene." Bull.Chem.Soc.Jpn.,. 64. 366-374 (1991)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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