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2003 Fiscal Year Final Research Report Summary

STUDY OF POLYMER-SUPPORTED DESS-MARTIN HYPERVALENT IODINE REAGENT

Research Project

Project/Area Number 13554028
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
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)

Co-Investigator(Kenkyū-buntansha) KAIHO Tasuo  Mitsui Chemicals Co., Material Chemicals Lab., Chief Researcher, 有機機能材料研究所, 主席研究員
YAMAGUCHI Kentaro  Chiba University, Chemical Analysis Center, Associate Professor, 分析センター, 助教授 (50159208)
Project Period (FY) 2001 – 2003
KeywordsAlcohol / Ketone / Aldehyde / Environmental Benign / Polymer-supported Hypervalent Iodine / リサイクル / カルボン酸
Research Abstract

Primary and secondary alcohols were successfully oxidized to the corresponding aldehydes and ketones at room temperature in good yields, respectively, with poly[4-(diacetoxyiodo)styrene] (PSDIB) in the presence of TEMPO (cat.) in acetone, as an environmentally friendly method. Here, polymer-supported hypervapent iodine was quantitatively recovered by simple filtration from the reaction mixture, and PSDIB was regenerated by treatment with peracetic acid and reused successfully. The previous methods such as Swern oxidation and Dess-Martin oxidation may be substituted by the present method, since the present oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones, respectively, is effective and secure as an operationally simple and environmentally benign method, and can be used for the synthesis of pharmaceutical and agrochemical substances

  • Research Products

    (45 results)

All Other

All Publications (45 results)

  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Novel Preparation and Reactivity of Poly[4-hydroxy-(tosyloxy)iodo]styrene"Synlett. 22-24 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A.Ryokawa, H.Togo: "Synthetic Use of 1,1,2,2-Tetraphenyldisilane for the Preparation of Biaryls Through the Intramolecular Free Radical ipso-Substitution of N-(2-"Tetrahedron. 57. 5915-5921 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] "Synthetic Use of Poly[4-hydroxy(tosyloxy)iodo]styrenes"J.Org.Chem.. 66. 6174-6177 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Katohgi, H.Togo: "Oxidatively Sonochemical Dealkylation of Various N-Alkylsulfonamides to Free Sulfonamides and Aldehydes"Tetrahedron. 57. 7481-7486 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Togo, M.Katohgi: "Synthetic Uses of Organohypervalent Iodine Compounds Through Radical Pathways"Synlett. 565-581 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Togo, M.Sugi, K.Toyama: "1,1,2,2-Tetraphenyldisilane (TPDS) as a New Diversified Radical Reagent"Comptes Rendus Serie IIc. 539-546 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sugi, H.Togo: "Environmentally Friendly TPDS-Mediated Free Radical Ring Expansion of α-Haloalkyl Cyclic β-Keto Esters"Tetrahedron. 58. 3171-3175 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Nabana, H.Togo: "Reactivity of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for α-Tosyloxylation and α-phosphoryloxylation of Ketones"J.Org.Chem.. 67. 4362-4365 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sakuratani, H.Togo: "Polymer-Supported Hypervalent Iodine Reagents"Synlett. 1966-1975 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄: "環境調和型化学変換試剤:高分子リサイクル型超原子価ヨウ素酸化剤の開発と展開"エコインダストリー(Eco Industry). 7. 5-18 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄, 櫻谷憲司: "高性能ポリマー型酸化試剤"化学と工業(日本化学会誌). 55. 1018-1020 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 22-23 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄: "環境に優しいラジカル反応試剤TPDSを用いた有機反応"ファインケミカル. 44-53 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sakuratani, Hideo Togo: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide with Polymer-supported Hypervalent Iodine Reagents."ARKIVOC. 11-20 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Misu, H.Togo: "Novel Preparation of 2,1-Benzothiazine Derivatives from Sulfonamides with [Hydroxy(tosyloxy)iodo]arenes"Org.Biomol.Chem.. 1. 1342-1346 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Togo, T.Hirai: "Environmentally-Friendly Wohl-Ziegler Bromination : Ionic-Liquid Reaction and Solvent-Free Reaction"Synlett. 702-704 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Ueno, T.Nabana, H.Togo: "Novel Oxidative a-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid, and Its Synthetic Application for the Direct"J.Org.Chem.. 68. 6424-6425 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sugi, D.Sakuma, H.Togo: "Zinc- and Indium-mediated Ring-Expansion Reaction of a-Halomethyl Cyclic b-Keto Esters in Aqueous Alcohol"J.Org.Chem.. 68. 7629-7633 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄: "有機フリーラジカルの化学"講談社サイエンティフィク. 187 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄: "有機反応のしくみと考え方"講談社サイエンティフィク. 273 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hideo Togo: "Advanced Free Radical Reactions for Organic Synthesis"Elsevier Science. 258 (2004)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 東郷秀雄: "実験化学講座 第5版,19巻 2章"ラジカル反応""丸善. 43 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Novel Preparation and Reactivity of Poly[4-hydroxy-(tosyloxy)iodo]-styrene"Synlett. 22-24 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A.Ryokawa, H.Togo: "Synthetic Use of 1,1,2,2-Tetraphenyldisilane for the Preparation of Biaryls Through the Intramolecular Free Radical ipso-Substitution of N-(2-Bromoaryl)arenesulfonamides"Tetrahedron. 57. 5915-5921 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Synthetic Use of Poly[4-hydroxy(tosyloxy)iodo]styrenes"J.Org.Chem.. 66. 6174-6177 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Katohgi, H.Togo: "Oxidatively Sonochemical Dealkylation of Various N-Alkylsulfonamides to Free Sulfonamides and Aldehydes"Tetrahedron. 57. 7481-7486 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo, M.Katohgi: "Synthetic Uses of Organohypervalent Iodine Compounds Through Radical Pathways"Synlett. 565-581 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo, M.Sugi, K.Toyama: "1,1,2,2-Tetraphenyldisilane (TPDS) as a New Diversified Radical Reagent"Compt.Rend.Serie IIc. 539-546 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sugi, H.Togo: "Environmentally Friendly TPDS-Mediated Free Radical Ring Expansion of a-Haloalkyl Cyclic b-Keto Esters"Tetrahedron. 58. 3171-3175 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Nabana, H.Togo: "Reactivity of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for a-Tosyloxylation and a-phosphoryloxylation of Ketones"J.Org.Chem.. 67. 4362-4365 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sakuratani, H.Togo: "Environmentally Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 22-23 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo, K.Sakuratani: "Polymer-Supported Hypervalent Iodine Reagents"Synlett. 1966-1975 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Environmentally Benign Reagents : Study of Polymer-supported Recyclable Hypervalent Iodine Reagents (Japanese)"Eco Industry. 7. 5-18 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Organic Free Radical Reactions with TPDS (Japanese)"Finechemicals. 44-53 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sakuratani, Hideo Togo: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide with Polymer-supported Hypervalent Iodine Reagents"ARKIVOC. 11-20 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Misu, H.Togo: "Novel Preparation of 2,1-Benzothiazine Derivatives from Sulfonamides with [Hydroxy(tosyloxy)iodo]arenes"Org.Biomol.Chem.. 1. 1342-1346 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sakuratani, H.Togo: "Environmentally Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo, T.Hirai: "Environmentally-Friendly Wohl-Ziegler Bromination : Ionic-Liquid Reaction and Solvent-Free Reaction"Synlett. 702-704 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Ueno, T.Nabana, H.Togo: "Novel Oxidative a-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid, and Its Synthetic Application for the Direct Preparation of Heteroaromatics"J.Org.Chem.. 68. 6424-6425 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sugi, D.Sakuma, H.Togo: "Zinc-and Indium-mediated Ring-Expansion Reaction of a-halomethyl Cyclic b-Keto Esters in Aqueous Alcohol"J.Org.Chem.. 68. 7629-7633 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Organic Free Radical Reactions (Japanese)"Kohdansha. 1-187 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Mechanism of Organic Reactions"Kohdansha. 1-271 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Radical Reactions in Organic Synthesis (Japanese) 19"Maruzen. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Togo: "Advanced Free Radical Reactions for Organic Synthesis"Elsevier Science. 1-258 (2004)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2005-04-19  

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