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Study on the Novel Radical Reactions with Hypervalent Iodine Compounds

Research Project

Project/Area Number 06640762
Research Category

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

Allocation TypeSingle-year Grants
Research Field 物質変換
Research InstitutionChiba University

Principal Investigator

TOGO Hideo  Chiba University, Department of Chemistry Faculty of Science, Associate Professor, 理学部, 助教授 (60217461)

Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1995: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1994: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsRadical reaction / Carbon-centered radical / Oxygen-centered radical / Nitrogen-centered radical / (Diacyloxyiodo) arene / Radical cyclization / ラジカルアミネーション / 高配位ヨウ素化合物 / ラジカルアルコキシレーション / スルフィド / 光照射反応 / ラクトン / カルボン酸 / 脱炭酸
Research Abstract

Radical reactions are one of the most useful methods for organic synthesis. Therefore, the study on the novel radical reactions with trivalent iodine compounds has been carried out. As a result, it was found that (diacyloxyiodo) arenes which has electron-donating group on a aromatic ring accelerated the radical reactivities under the irradiation with tungsten lamp as shown below,
1) conversion of carboxylic acids to the corresponding sulfides in the presence of disulfides,
2) conversion of aromatic carboxylic acids to the corresponding gamma-or delta-lactones,
3) conversion of alcohols bearing a aromatic ring to the corresponding cyclic ethers,
4) conversion of amines bearing a aromatic ring to the corresponding cyclic amines,
These reactions proceed via the formation of carbon-, oxygen-, and nitrogen-centered radicals to give the products with a simple operation in good yields. In nature, there are many kinds of important cyclic compounds containing oxygen and nitrogen atoms. Therefore, the present method is very useful for the preparation of these natural products. These results were published in three international Journals in 1995, and the other papers are in preparation for the contribution to the Journals.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] H.Togo, K.Hayashi, and M.Yokoyama,: "Radical Alkylation of Heteroaromatic Bases with Polysilane Compounds" Bulletin of The Chemical Society of Japan. 67. 2522-2527 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Ishigami, H.Togo, and M.Yokoyama,: "Reactivity of Carbocyclic Four-Membered Radicals for the Preparation of Carbocyclic Analogues of Oxetanocins" Journal of The Chemical Society, Perkin 1,. 2407-2412 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo, S.Ishigami, M.Fujii, T.Ikuma,and M.Yokoyama,: "Synthesis of C-Nucleosides via Radical Coupling Reaction" Journal of The Chemical Society,Perkin 1,. 2931-2942 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo, T.Muraki, and M.Yokoyama,: "Preparation of Adamantyl Sulfides with [Bis (adamantanecarboxy) iodo] arenes and Disulfides" Synthesis,. 155-157 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo, R.Taguchi, and M.Yokoyama,: "Reactivities of [Bis (adamantanecarboxy) iodo] arenes in Substitution and Addition Reactions" Jouranal of The Chemical Society,Perkin 1,. 2135-2139 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo,T.Muraki,and M.Yokoyama,: "Remote Functionalization (1) : Synthesis of g-and d-Lactones from Aromatic Carboxylic Acids" Tetrahedron Letters. 36. 7089-7092 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hideo Togo, Ken Hayashi, and Masataka Yokoyama: "Radical Alkylation of Heteroaromatic Bases with Polysilane Compounds" Bulletin of The Chemical Society of Japan. 67. 2522-2527 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Sachiko Ishigami, Hideo Togo, and Masataka Yokoyama: "Reactivity of Carbocyclic Four-membered Radicals for the Preparation of Carbocyclic Analogues of Oxetanocins" Journal of The Chemical Society, Perkin. 1. 2407-2412 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hideo Togo, Sachiko Ishigami, Misa Fujii, Toshihiro Ikuma, and Masataka Yokoyama: "Synthesis of C-Nucleosides via Radical Coupling Reaction" Journal of The Chemical Society, Perkin. 1. 2931-2942 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hideo Togo, Takahito Muraki, and Masataka Yokoyama: "Preparation of Adamantyl Sulfides with [Bis (adamantanecarboxy) iodo] arene and disulfides" Synthesis. 155-157 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo, Rie Taguchi, and Masataka yokoyama: "Reactivities of [Bis (adamantanecarboxy) iodo] arenes in Substitution and Addition reactions" Journal of The Chemical Society, Perkin. 1. 2135-2139 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hideo Togo, Takahito Muraki, and Masataka Yokoyama: "Remote Functionalization : Synthesis of gamma-and delta-Lactones from Aromatic Carboxylic Acids" Tetrahedron Lettes. 36. 7089-7092 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Togo,K.Hayashi,and M.Yokoyama,: "Radical Alkylation of Heteroaromatic Bases with Polysilane Compounds" Bulletin of The Chemical Society of Japan. 67. 2522‐2527 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Ishigami,H.Togo,and M.Yokoyama,: "Reactivity of Carbocyclic Four‐Membcred Radicals for the Preparation of Carbocyclic Analogues of Oxetanocins" Journal of The Chemical Society, Perkin 1,. 2407‐2412 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Togo,S.Ishigami,M.Fujii,T.Ikuma,and M.Yokoyama,: "Synthesis of C‐Nucleosides via Radical Coupling Reaction" Journal of The Chemical Society, Perkin 1,. 2931‐2942 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Togo,T.Muraki,and M.Yokoyama,: "Preparation of Adamantyl Sulfides with[Bis(adamantanecarboxy)iodo]arenes and Disulfides" Synthesis,. 155‐157 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Togo,R.Taguchi,and M.Yokoyama,: "Reactivities of[Bis(adamantanecarboxy)indo]arenes in Substitution and Addition Reactions" Journal of The Chemical Society, Perkin 1,. 2135‐2139 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Togo,T.Muraki,and M.Yokoyama,: "Remote Functionalization(1): Synthesis of g‐and d‐Lactones from Aromatic Carboxylic Acids" Tetrahedron Letters. 36. 7089‐7092 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Yokoyama,S.Hirano,T.Hachiya,and H.Togo.: "Thermolysis and Photolysis of Sugar Diazides" Chemistry Letters. 1107-1110 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Togo,K.Hayashi,and M.Yokoyama,: "Radical Alkylation of Heteroaromatic Bases with Polysilane Compounds" Bulletin of The Chemistry Sociery Japan. 67. 2522-2527 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.M.T.Truong-Nguyen,H.Togo,and M.Schlosser,: "A Fluoroisopreylation Sequence Employing 2-Fluoroalkenal Derived Azomethincs AS Key Intermediates." Tetrahedron. 50. 7827-7836 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ishigami,H.Togo,and M.Yokoyama,: "Reactivity of Carbocyclic Four-Membered Radicals for the Preparation of Carbocyclic Analogues of Oxetanocins" Journal of The Chemical Society,Perkin 1. 2407-2412 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Togo,S.Ishigami,M.Fujii,and M.Yokoyama: "Synthesis of C-Nuclcosides via Radical Conpling Reaction" Journal of The Chemical Society,Perkin 1. 2931-2942 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Yokoyama and H.Togo,: "Transformation of Alkyl N-(Vinyloxy)bcnzimidates to Alkyloxazoles. Mechanism and Extension" Bulletin of The Chemical Society of Japan. 67. 2219-2226 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Togo,: "`Nitro Compounds`in “Synthetic Organic Chemistry"" Marcel Deakker Inc.,New York, 100 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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