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Molecular Recognition of Reactive Species : Asymmetric Photoamination

Research Project

Project/Area Number 10650837
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 InstitutionMiyazaki University

Principal Investigator

YASUDA Masahide  Miyazaki University, Associate Professor, 工学部, 教授 (00174516)

Co-Investigator(Kenkyū-buntansha) SHIRAGAMI Tsutomu  Miyazaki University Associate Professor, 工学部, 助教授 (60235744)
志摩 健介  宮崎大学, 工学部, 教授 (20029862)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2000: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1999: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1998: ¥2,000,000 (Direct Cost: ¥2,000,000)
KeywordsBenzocycloalkenes / Photoamination / Diakoxybinaphthols / Asynmetric recognization / Chiral π donors / Benzylidene tartrate / アミノ化反応 / アリールシクロプロパン / ベンゾシクロアルケン / ベンゾシクロヘプテン / ベンジリデン酒石鹸エステル / ジベンゾ[a,d]シクロヘブテンイミン
Research Abstract

(1) Redox-Photosensitization : In order to perform the photoamination of the substrates such as benzocycloalkenes, arylcyclopropanes, and quadricyclane that has no or weak absorption at near-ultraviolet regions, we applied the photosensitization using biphenyl derivatives and 2, 2-dialkoxy-1, 1'-naphthalene as the redox-photosensitizer. As the results, the photoamination of the substrates proceeded efficiently without the cosumption of the sensitizer.
(2) Photoamination in the presence of chiral π-donors : In order to attempt the asymmetric photoamination, the photoamination in the presence of chiral π-donors have been performed. When chiral benzyl menthyl ethers were used, the specific rotatory of the aminated products depended on the reaction temperature and the chiral π-donors used.
(3) Intercalation of chiral π-donors into β-cyclodextrins : Fluorescence spectral changes of (-)-and (+)-dialkyl 2-aryl-1, 3-dioxolane-4, 5-dicarboxylates having the methoxyphenyl group and the rigid conformation by the addition of b-cyclodextrin were investigated. In some cases, the enhancing effects on the fluorescence were different in (+)-and (-)-isomeres.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] M.Yasuda: "Photoamination of Alkenylnaphthalenes with Ammonia via Electron Transfer"Bull.Chem.Soc.Jpn. 71. 1655-1660 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photochemistry of Flavins in Micells : Specific Effects of Anionic Surfactants on the Monomerization of Thymine Cyclobutane Dimers Photosensitized by Tetra-O-acyl Riboflavins"Photochem.Potobiol.A : Chemistry. 67. 192-197 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamashita: "Benzophenone-Photosensitized Alkylation of Arylalkenes with Acetone, Dimethyl Sulfoxide, and Their Related Compounds in the Presence of Tert-Butylamine"J.Photochmem.Photobiol.A : Chemistry. 118. 165-171 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Solvent Parameter Based on the Exciplex Emission of (2-Naphthoxy) polyalkyl p-Cyanobenzoates"J.Photochmem.Photobiol.A : Chemistry. 121. 149-155 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photoamination of 1, 2-Diarylcylopropanes Using 2, 2'-Dialkoxy-1, 1'-binaphthalene as Redox-Photosensitizer"Chem.Lett.. 1269-1270 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photoamination of Alkenylnaphthalenes with Ammonia via Electron Transfer"Bull.Chem.Soc.Jpn.. 71. 1655-1660 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photochemistry of Flavins in Micells : Specific Effects of Anionic Surfactants on the Monomerization of Thymine Cyclobutane Dimers Photosensitized by Tetra-O-acyl Riboflavins"Photochem.Photobiol.A : Chemistry. 67. 192-197 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamashita: "Benzophenone Photosensitized Alkylation of Arylalkenes with Acetone, Dimethyl Sulfoxide, and Their Related Compounds in the Presence of Tert-Butylamine"J.Photochem.Photobiol.A : Chemistry. 118. 165-171 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Solvent Parameter Based on the Exciplex Emission of (2-Naphthoxy) polyalkyl p-Cyanobenzoates"J.Photochem.Photobiol.A : Chemistry. 121. 149-155 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photoamination of 1, 2-Diarylcylopropanes Using 2, 2'-Dialkoxy 1, 1'-binaphthalene as Redox Photosensitizer"Chem.Lett.. 1269-1270 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yasuda: "Photoamination of 1,2-Diarylcyclopropanes Using 2,2'-Dialkoxy-1,1'-binaphthalene as Redox-Photosensitizer"Chem.Lett.. 12号. 1269-1270 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Yasuda: "Solvent Parameter Based on the Exciplex Emission of(2-Naphthoxy)polyoxalkyl p-Cyanobenzoates"J.Photochem.Photobiol.A Chemistry. 121巻. 149-155 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Yasuda: "Photochemistry of Flavins in Micelles: Specific Effects of Anionic Surfactants on the Monomerization of Thymine Cyclobutane Dimers Photosensitized by Tetra-O-acyl Riboflavines" Photochem.Photobiol.67巻、2号. 192-197 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Yasuda: "Photoamination of Alkenylnaphthalene with Ammonia via Electron Transfer" Bull.Chem.Soc.Jpn.71巻、7号. 1655-1660 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Yamashita: "Bezophenone-Photosensitized Alkylation of Arylakenes with Acetone, Dimethyl Sulfoxide, and Their Related Compounds in the Presence of tert-Butylamine" J.Photochem.Photobiol.A.Chem.118巻、3号. 165-171 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Yasuda: "Solvent Parameter based on the exciplex emission of (2-naphthoxy) polyoxalkyl p-cyanobenzoate" J.Photochem.Photobiol.A.Chem.(in press). (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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