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Synthetic Application of Photochemical Electron Transfer in Solvents with Relatively Low Polarity.

Research Project

Project/Area Number 01550655
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionMiyasaki University

Principal Investigator

SHIMA Kensuke  宮崎大学, 工学部, 教授 (20029862)

Co-Investigator(Kenkyū-buntansha) NAKABAYASHI Kenichi  宮崎大学, 教育学部, 講師 (60201670)
YASUDA Masahide  宮崎大学, 工学部, 助教授 (00174516)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1990: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsPhotochemical Electron Transfer / Photoamination / Arenes / Solvent with Relatively Low Polarity / Ring-Cleavage Reactions / Oxetanes, / Exciplexes
Research Abstract

(1) The photoamination of phenanthrene with propylamine in the presence of p-dicyanobenzene was investigated in solvents with relatively low polarity such as 1, 2-dimethoxyethane, tetrahydrofuran, and 1, 4-dioxane. The photoamination in the presence of Et_4NBF_4 occurred to give 9-proplyamino-9, 10-dihydrophenanthrene, while photoamination in the absence of the salt did not occur al all. We assume the mechanism for the photoamination via salt-induced charge separation of the exciplexes between phenanthrene and p-dicyanobenzene into ion radicals.
Also, the photoamination of naphthalenes, 2, 3-dimethylnaphthalene, and anthracene proceeded in the presence of the salt to give aminated products.
(2) The stereochemistry of the photoamination was elucidated for phenanthrene derivatives. It is found that the amine and ammonia add to the arenes in the trans manner predominantly. The stereoselectivities of amination did not depend on solvent polarity.
(3) Photochemical rig-cleavage reaction of 2, 2-diaryloxetanes in the presence of triethylamine proceeded in hexane to give 1, 1-diarylethenes selectively. The photoreaction was suggested to occur via exciplex between the oxetane and triethylamine.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] 保田 昌秀: "エキシプレックスを経由するフェナントレンの光アミノ化反応に対する塩効果の速度論的解析" 日本化学会論. 1292-1298 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 保田 昌秀: "光電子移動反応を経由するフェナントレン類のアンモニアおよびアミンによる直接的光アミノ化反応に対する溶媒効果" 旭硝子工業技術奨励会研究報告. 54. 263-269 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 志摩 健介: "ナフトアルデヒド類の2,3ージメチルー2ーブテンへの光付加ならびに生成オキセタンの光誘起環開裂反応" 宮崎大学工学部研究報告. 36. 23-29 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 保田 昌秀: "低極性溶媒中での芳香族炭化水素の光アミノ化反応 ーエキシプレックスの電荷分離に対する塩効果" 旭硝子財団研究報告書. 56. 103-109 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Kinetic Analysis of Salt Effect on Photoamination of Phenanthrene via Exciplex Intermediate" Nippon Kagakukaishi. 1292-1298 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Solvents Effect on Direct Photoamination of Phenanthrene Derivatives with Ammonia and Amines via Photoelectron Transfer" Rep. Asahi Glass Found. Ind. Tehnol.54. 263-269 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenichi Nakabayashi: "Photochemical Ring-Cleavage Reactions of 2, 2-Diaryloxetanes in the Presence of Electron Donor." Bull. Chem. Soc. Jpn.62. 2733-2735 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kensuke Shima: "Photoaddition of Naphthaldehydes to 2, 3-Dimethy1-2-butene and Photoinduced Ring-Cleavage Reactions of the Oxetanes" Bull. Fac. Miyazaki Univ.26. 23-29 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Masahide Yasuda: "Photoamination of Arenes in Solvents of Relatively Low Polarity. Salt Effects on Charge Separation of Exciplex" Rep. Asahi Glass Found.56. 103-109 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 保田 昌秀: "エキシプレックスを経由するフェナントレンの光アミノ化反応に対する塩効果の速度論的解析" 日本化学会誌. 1292-1298 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] 保田 昌秀: "光電子移動反応を経由するフェナントレン類のアンモニアおよびアミンによる直接的光アミノ化反応に対する溶媒効果" 旭硝子工業技術奨励会研究報告. 54. 263-269 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenichi Nakabayashi: "Photochemical RingーCleavage Reactions of 2,2ーDiarylーoxetanes in the presence of Electron Doror." Bull.Chem.Soc.Jpn.62. 2733-2735 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] 志摩 健介: "ナフトアルデヒド類の2.3ージメチルー2ーブチンへの光付加ならびに生成オキセタンの光誘起環開裂反応" 宮崎大学工学部研究報告. 36. 23-29 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 保田 昌秀: "低極性溶媒中での芳香族炭化水素の光アミノ化反応ーエキシプレックスの電荷分離に対する塩効果" 旭硝子財団研究報告書. 56. 103-109 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenichi Nakabayashi: "Photochemical Ring-Cleavage Reactions of 2,2-Diaryl-oxetanes in the Presence of Electron Donor" Bull.Chem.Soc.Jpn. 62. 2733-2735 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 保田昌秀: "エキシプレックスを経由するフェナントレンの光アミノ化反応に対する塩効果の速度論的解析" 日本化学会誌. 1292-1298 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 保田昌秀: "光電子移動反応を経由するフェナントレン類のアンモニアおよびアミンによる直接的光アミノ化反応に対する溶媒効果" 旭硝子工業技術奨励会研究報告. 54. 263-269 (1989)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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