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1986 Fiscal Year Final Research Report Summary

Development of new organic reactions including electron transfer process

Research Project

Project/Area Number 60303016
Research Category

Grant-in-Aid for Co-operative Research (A)

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

Principal Investigator

SHONO Tatsuya  Faculty of Engineering, Kyoyo University, Professor, 工学部, 教授 (80025858)

Co-Investigator(Kenkyū-buntansha) MATSUMURA Yoshihiro  Faculty of Engineering, Kyoto University, Associate Professor, 工学部, 助教授 (60026309)
MURAKAMI Yukito  Faculty of Engineering, Kushu University, Professor, 工学部, 教授 (30037717)
YAMAMURA Shosuke  Faculty of Science and Technology, Keio University, Professor, 理工学部, 教授 (40076708)
OSA Tetsuo  Pharmaceutical Institute, Tohoku University, Professor, 薬学部, 教授 (10010753)
SUGINOME Hiroshi  Faculty of Engineering, Hokkaido University, Professor, 工学部, 教授 (00000779)
Project Period (FY) 1985 – 1986
KeywordsElectron transfer reaction / Organic reaction / Reduction / Oxidation / Electroorganic reaction / 光反応
Research Abstract

Electron transfer reactions often play important roles in organic reactions since an electron itself behaves as a reagent. Thus, development of new organic reactions including electron transfer process has been studied in this project. Following results were obtained in this project.
1. New method for the synthesis of <beta> -lactams, bastadin-6, piperazinomycin, olean-11-ene-o <beta> , 28-olide, the preparation of new acyl anion equivalents, and the formation of a novel electrogenerated base have been found using electroorganic reaction as a key reaction.
2. Epoxidation of olefins using electrochemically generated <O^(-.)_2> , stereo selective cyclization of anodically formed nitrogen radicals, and indirect anodic oxidation of alcohols using mediator have been established.
3. Cathodic rearrangement of <beta> -halo esters using vitamin <B_(12)> , and a new method for the oxidation of alcohols using ZnO anode have been found.
4. Stereo selective allylation, double functionalization of olefins catalyzed by Pd, and the insertion of CO to aldehydes using Co catalysts have been established.
5. Photo chemical functionalization of nucleo acid and cleavage of Si-C bond.
6. One-electron oxidation of aromatic compounds by <alpha> -keto kations has been studied.

  • Research Products

    (39 results)

All Other

All Publications (39 results)

  • [Publications] Tatsuya Shono;Naoki Kise;Mitsuharu Masuda;TaKeshi Suzumoto: J.Org.Chem.50. 2527-2533 (1985)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Miwako Mori;Yasuhiro Uozumi;Yoshio Ban: J.Chem.Soc.,Chem.Commun.841-842 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masao Tokuda;Yasufumi Yamada;Toshiya Takagi;Hiroshi Suginome;Akio Furusaki: Tetrahedron. 43. 281-296 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nagao Kobayashi;Hiroshi Saiki;Tetsuo Osa: Chemistry Letters. 1917-1920 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakadaira;N.Komatsu;H.Sakurai: Chemistry Lettters. 1781-1782 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] Yoshikazu Shizuri;Kazuharu Suyama;Shosuke Yamamura: J.Chem.Soc.,Chem.Commun.63-64 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Kuniaki Tatsuta;Yoshiyuki Kobayashi;Mitsuhiro Kinoshita: Chemistry Letters. 187-190 (1987)

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      「研究成果報告書概要(和文)」より
  • [Publications] Makoto Nakazawa;Yasushi Mizobe;Yoichi Matsumoto;Yasuzo Uchida;Meguru Tezuka;Masanobu Hidai: Bull.Chem.Soc.Jpn.59. 809-814 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Toshio Fuchigami;Akira Sato;Tsutomu Nonaka: Chemistry Express. 1. 363-366 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] 加藤民彦,前川悦朗,藤嶋昭,本多健一: 日本化学会誌.

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      「研究成果報告書概要(和文)」より
  • [Publications] T.Kitagawa;K.Takeuchi;O.Murai;S.Matsui,T.Inoue;M.Nishimura;Kunio Okamoto: J.Chem.soc.,Perkin Trans.2. 1987-1995 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] T.Iyoda;M.Ando;T.Kaneko;A.Ohtani;T.Shimidzu;Kenichi Honda: Tetrahedron Letters. 27. 5633-5636 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Tamio Hayashi;Akihiro Yamamoto;Yoshihiko Ito: J.Chem.Soc.,Chem.Commun.1090-1092 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Tatsuya Shono;Yoshihiro Matsumura;Susumu Katoh;Kenji Inoue;Yonetatsu Matsumoto: Tetrahedron Letters. 27. 6083-6086 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tamaru;M.Hojo;H.Higashimura;Z.Yoshida: Angew.Chem.Int.Ed.Engl.25. 735-737 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Isao Saito;Hideyuki Ikehira;Ryuichiro Kasatani;Masakazu Watanabe;Teruo Matsuura: J.Am.Chem.Soc.108. 3115-3117 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tatsuya Shono;Osamu Ishige;Hiroshi Uyama;Shigenori Kashimura: J.Org.Chem.51. 546-549 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Shinji Murai: J.Mol.Cat.(in press).

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      「研究成果報告書概要(和文)」より
  • [Publications] Yukito Murakami;Y.Hisaeda;T.Ozaki;T.Tashiro;T.Ohno;Y.Tani;Y.Matsuda: Bull.Chem.Soc.Jpn.60. 311-324 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tatsuya Shono,* Naoki Kise, Mitsuharu Masuda, and Takeshi Suzumoto: "Chain Reactions Induced by Cathodic Reduction" J. Org. Chem.50. 2527-2533 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Miwako Mori, Yasuhiro Uozumi, and Yoshio Ban: "Total Synthesis of Neothramycin" J. Chem. Soc., Chem. Commun.841-842 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Maso Tokuda, Yasufumi Yamada, Toshiya Takagi, Hiroshi Suginome, and Akio Furusaki: "Cyclization of Aminyl Radical Generated by Anodic Oxidation of Lithium Alkenylamides. Stereo- and Regioselective Synthesis of cis-1-Alkyl-2,5-disubstituted pyrrolidines" Tetrahedron. 43. 281-296 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nagao Kobayashi, Hiroshi Saiki, and Tetsuo Osa: "Catalytic Electroreduction of Molecular Oxygen Using [5,10,15,20-Tetrakis(1-methylpyridiunium-4-yl)porhinato] Manganese" Chemistry Letters. 1917-1920 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakadaira, N. Komatsu, and H. Sakurai: "Chlorinative Cleavage of Permethylpolysilanes Initiated by Photoinducted Charge Transfer" Chemistry Letters. 1781-1782 (1985)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshikazu Shizuri, Kazuharu Suyama, and Shosuke Yamamura*: "Total Synthesis of ( <-!+> )-Helminthosporal" J. Chem. Soc., Chem. Commun.63-64 (1986)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Kuniaki Tatsuta, Yoshiyuki Kobayashi, and Mitsuhiro Kinoshita: "An Enantioselective Synthesis of a Macrolide from the Polyketide Lactone Derived from Oleandomycin" Chemistry Letters. 187-190 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Makoto Nakazawa, Yasushi Mizobe, Yoichi Matsumoto, Yasuzo Uchida, Meguru Tezuka, and Masanobu Hidai: "Electrochemical Reduction of Carbon Dioxide Using Iron-Sulfur Clusters as Catalyst Precursors" Bull. Chem. Soc. Jpn.59. 809-814 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Toshio Fuchigami, Akira Sato, and Tsutomu Nonaka: "Electroreductive Asymmetric Alkylation" Chemistry Express. 1. 363-366 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tamihiko Kato, Etsuro Maekawa, Akira Fujishima, and Ken'ichi Honda: "Oxidation of Alcohols on Zinc Oxide Photo-Anode" Nippon Kagaku Kaishi.

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  • [Publications] Toshikazu Kitagawa, Ken'ichi Takeuchi, Osamu Murai, Shin Matsui, Takeshi Inoue, Makoto Nishimura, and Kunio Okamoto*: "One-electron Oxidation of Closed-shell Molecules. Part 4. Acid-induced Oxidative Cleavage of Substituted 1,2,2,2-Tetraphenylethanones (Benzpinacolones) with Diaroyl Peroxides" J. Chem. Soc., Perkin Trans. 2. 1987-1995 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tomokazu Iyoda, Masayoshi Ando, Takehira Kaneko Akira Ohtani, Takeo Shimidzu, and Kenichi Honda: "Electrochemical Polymerization in Langmuir-Blodgett Film of New Amphiphilic pyrrole Derivatives" Tetrahedron Letters. 27. 5633-5636 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tamio Hayashi, Akihiro Yamamoto, and Yoshihiko Ito: "Kinetic Resolution of Racemic Allyl Acetates in Asymmetric Allylic Alkylation Catalyzed by a Chiral Ferrocenylphosphine-Palladium Complex" J. Chem. Soc., Chem. Commun.1090-1092 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tatsuya Shono, Yoshihiro Matsumura, Susumu Katoh, Kenji Inoue, and Yonetatsu Matsumoto: "Electrooxidative Rearrangement of Tosylamino Group: Facile Synthesis of <alpha> -Amino Aldehydes from Primary Amines" Tetrahedron Letters. 27. 6083-6086 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] <Pd^(II)> -Catalyzed Regioselective Arylchlorination and Oxyarylation of Unsaturated Alcohols: "Y. Tamaru, M. Hojo, H. Higashimura, and Z. Yoshida" Angew. Chem. Int. Ed. Engl.25. 735-737 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Isao Saito, Hideyuki Ikehira, Ryuichiro Kasatani, Masakazu Watanabe, and Teruo Matsuura: "Selective Deoxygenation of Secondary Alcohols by Photosensitized Electron-Transfer Reaction" J. Am. Chem. Soc.108. 3115-3117 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tatsuya Shono, Osamu Ishige, Hiroshi Uyama, and Shigenori Kashimura: "A Novel Base Useful for Synthesis of Esters and Macrolides" J. Org. Chem.51. 546-549 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Masayuki Yoshikawa, Nobutoshi Murakami, Toshio Taniyama, Yoshihiro Hamamoto, Takahiko Nakae, and Isao Kitagawa: "Intramolecular Carbonyl-Mediated Electrochemical Oxidation: Skeletal Rearrangement of an Oleanene Triterpene and Its Oligoside"

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shinji Murai: "Silylcobalt Carbonyl and New Catalytic Reactions" J. Mol. Cat.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yukito Murakami,* Yoshio Hidaeda, Toshiaki Ozaki, Takako Tashiro, Teruhisa Ohno, Yutaro Tani, and Yoshihisa Matsuda: "Hydrophobic Vitamin <B_(12)> . V. Electrochemical Carbon-Skeleton Rearrangement as Catalyzed by Hydrophobic Vitamin <B_(12)> : Reaction Mechanisms and Migratory Aptitude of Functional Groups" Bull. Chem. Soc. Jpn.60. 311-324 (1987)

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      「研究成果報告書概要(欧文)」より

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Published: 1988-11-09  

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