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Study on the Novel Radical Reagents Using the Specificity of Hypervalent Iodine Compounds

Research Project

Project/Area Number 08640670
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

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

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1997: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1996: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsRadical Reactions / Hypervalent Iodine Compounds / Carbon-centered Radical / Oxygen-centered Radical / Nitrogen-centered Radical / 炭素-炭素結合形成 / 酸素ラジカル / 炭素-酸素結合形成 / 酸素-炭素結合形成
Research Abstract

Radical reactions are one of the most useful methods for organic synthesis. Therefore, the study on the novel radical reactions with hypervalent iodine compounds has been carried out. Here, based on our study, the formation of carbon-centered radicals, oxygen-centered radicals, and nitrogen-centered radicals with hypervalent iodine compounds has been established. Especially, the formation of nitrogen-centered radicals from sulfonamides with hypervalent iodine compounds is very useful for the preparation of 1,2,3,4-tetrahydroquinoline derivatives and saccharin derivatives. Then, the present method was applied for the preparation of the key skeletons of biologically active compounds. These results were published in five international Journals and other three papers are in press.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] Hideo Togo, Masashi Katohgi, and Masataka Yokoyama: "Direct Prepartion of Saccharin Derivatives from amides with N-Methl(o-methyl)arenesulfonamides with (Diacetoxyiodo)" Synlett. 34. 131-132 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takahito Muraki, Hideo Togo, and Masataka Yokoyama: "Synthetic Use of 1-(p-Toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one:Iodination of Aromatic Rings" Synlett. 34(in press). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideo Togo, Takahito Muraki, Yoichiro Hoshina, and Masataka Yokoyama: "Formation and Synthetic Use of Oxygen-centered Radicals with (Diacetoxyiodo)arenes" Journal of The Chemical Society,Perkin Trans.1. 787-793 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Osamu Yamazaki, Hideo Togo, Genki Nogami, and Masataka Yokoyama: "Novel Water-Soluble Organosilane Compounds as a Reducing Agent in Aqueous Media" Bulletin of The Chemical Society of Japan. 70. 2519-2523 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Wei He, Hideo Togo, Hiroyuki Ogawa, and MasatakaYokoyama: "Studies on the Formation of Alkyl Radicals from Alkyl Aryl Tellurides and Their Application to the Synthesis of Carbocyclic C-Nucleoside Analogs" Heteroatom Chemistry. 8. 411-419 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takahito Muraki, Hideo Togo, and Masataka Yokoyama: "Hypervalent iodine Componds as Free Radical Precursors" Reviews on Heteroatom Chemistry. 17. 213-243 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideo Togo, Yoichiro Hoshina, and Masataka Yokoyama: "Cyclic Amination onto Aromatic Ring of Sulfornamides with (Diacetoxyiodo) arenes : Effect of Sulfonyl Group" Tetrahedron Letters. 34. 6129-6132 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takahito Muraki, Hideo Togo, and Masataka Yokoyama: "Remote Functionalization : Cyclic Alkoxylation onto Aromatic Ring via Radical Pathways" Tetrahedron Letters. 34. 2442-2444 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideo Togo, Takahito Muraki, Yoichiro Hoshina, and Masataka Yokoyama: "Formation and Synthetic Use of Oxygen-centered Radicals with (Diacetoxyiodo) arenes" Journal of Chemical Socity, Perkin Trans.1. 787-793 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Osamu Yamazaki, Hideo Togo, Genki Nogami, and Masataka Yokoyama: "Novel Water-Soluble Organosilane Compounds as a Reducing Agent in Aqueous Media" Bulletin of Chemical Society of Japan. 70. 2519-2523 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Wei He, Hideo Togo, Hiroyuki Ogawa, and Masataka Yokoyama: "Studies on the Formation of Alkyl Radicals from Alkyl Aryl Tellurides and Their Application to the Synthesis of Carbocyclic C-Nucleoside Analogs" Heteroatom Chemistry. 8. 411-419 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takahito Muraki, Hideo Togo, and Masataka Yokoyama: "Hypervalent iodine Compounds as Free Radical Precursors" Reviews on Heteroatom Chemistry. 17. 213-243 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideo Togo, Masashi Katohgi, and Masataka Yokoyama: "Direct Preparation of Saccharin Derivatives from N-Methyl (o-methyl) arenesulfonamides with (Diacetoxyiodo) arenes" Synlett. 131-132 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takahito Muraki, Hideo Togo, and Masataka Yokoyama: "Synthetic Use of 1- (p-Toluenesulfonyloxy) -1,2-benziodoxol-3 (1H) -one : Iodination of Aromatic Rings" Synlett. (in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] O.Yamazaki, H.Togo, G.Nogami, and M.Tokoyama: "Novel Water-Soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media" Bulletin of the Chemical Society of Japan. 70. 2519-2523 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] W.He, H.Togo, and M.Yokoyama: "Strategic Approach to C-Nucleosides via Sugar Anomeric Radical, Cation, and Anion with Sugar Tellurides" Tetrahedron Letters. 38. 5541-5544 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] W.He, H.Togo, H.Ogawa, and M.Yokoyama: "Studies on the Formation of Alkyl Radicals from Alyl Aryl Tellurides and Their Application to the Synthesis of Carbocyclic C-Nucleoside Analogs" Heteroatom Chemistry. 8. 411-419 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Muraki, H.Togo, and M.Yokoyama: "Hypervalent Iodine Compounds as Free Radical Precursors" Reviews on Heteroatom Chemistry. 17. 213-243 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Togo, T.Katohgi, and M.Yokoyama: "Direct Preparation of Saccharin Skeletons from N-Methyl (o-methyl) arenesulfonamides with (Diacetoxyiodo) arenes" Synlett. 131-132 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] O.Yamazaki, H.Togo, and S.Matsubayashi: "1,1,2,2-tetraphenyldisilane as a Diversified Radical Reagent" Tetrahedron Letters. 39(in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Muraki,H.Togo,and M.Yokoyama: "Remote Functionalization : Cyclic Alkoxylation onto Aromatic Ring via Radical Pathway" Tetrahedron letters. 37. 2441-2444 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Togo,Y.Hoshino,and M.Yokoyama: "Cyclic Amination onto Aromatic Ring of Sulfonamides with (Diacetoxyiodo) arenes : Effect of Sulfonyl Group" Tetrahedron Letters. 37. (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Yokoyama,M.Nomura,H.Togo,and H.Seki: "Coupling of Ribofuranosyl Fluoride and Iodoles" Journal of the Chemical Society,Perkin I. 2145-2149 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] W.He,H.Togo,H.Ogawa,and M.Yokoyama: "Studies on the Formation of AlkyI Radicals from AlkyI Tellurides and Their Application to the Synthesis of Carbocyclic C-Nucleoside Analogues" Heteroatom Chemistry. 8(in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Yogo,T.Muraki,Y.Hoshina,and M.Yokoyama: "Formation and Synthetic Use of Oxygen-centered Radicals with (Diacetoxyiodo) arenes" Journal of the Chemical Society,Perkin I. (in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 東郷秀雄、星名洋一郎、野上玄器、横山正孝: "三配位ヨウ素化合物の特性を活かした有機ラジカル反応" 有機合成化学協会誌. 55. 90-98 (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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