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Reaction control of cyclic ethers by new versatile catalysts and its application

Research Project

Project/Area Number 60430022
Research Category

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

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

Principal Investigator

MATSUDA Haruo  Osaka University, Faculty of Engineering Professor, 工学部, 教授 (20028963)

Co-Investigator(Kenkyū-buntansha) BABA Akio  Osaka University, Faculty of Engineering Associate Professor, 工学部, 助教授 (20144438)
MIYOSHI Noritaka  Osaka University, Faculty of Engineering Associate Professor, 工学部, 助教授 (80157700)
MURAI Shinji  Osaka University, Faculty of Engineering Professor, 工学部, 教授 (00029050)
蜷川 彰  大阪大学, 工学部, 助教授 (10029051)
Project Period (FY) 1985 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥35,000,000 (Direct Cost: ¥35,000,000)
Fiscal Year 1987: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1986: ¥8,000,000 (Direct Cost: ¥8,000,000)
Fiscal Year 1985: ¥25,000,000 (Direct Cost: ¥25,000,000)
Keywordsoxirane / isocyanate / carbodiimide / cycloaddition / regiocontrol / organotin halide complexes / 有機スズハライド錯体 / オキシラン / オキセタン / イソシアナート / オキサジノン / 3,4-ジ置換オキサゾリドン
Research Abstract

The cycloaddition of oxiranes with heterocumulenes such as isocyanates and carbodiimides has been ardently investigated. Although a variety of catalysts for this reaction have been reported, the problems such as low yields and severe reaction conditions have not been resolved as yet. Now, this our project has given one resolution in terms of developing novel catalysts; organotin iodide-Lewis base complexes(1), organotin iodide-onium halide salts complexes(2) and tetraphenylstibonium iodide(3). These catalysts very effectively promoted the cycloadditon of under very mild conditions to produce many kinds of heterocyclic compounds in excellent yield. Advantages and features of these catalysts are as follows(a-c);
(a) The cycloadditions complete within few hours at room temperature.
(b) The catalysts 1 and 2 selectively promote the -cleavage cycloaddition of monosubstituted oxiranes. On the contrary, the catalyst 3 promotes the -cleavage one which has been unsuccessful by conventional catalysts at all. The both reactions could be carried out for the same reactants under similar reaction conditions, and so these catalysts can be used compensationally.
(c) These catalysts are so nearly neutral that the oxiranes bearing labile substituents are applicable to this cycloaddition.

Report

(3 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • 1985 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] A.Baba: Tetrahedron Lett.26. 5167-5170 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Baba: Tetrahedron Lett. 27. 77-80 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I.Shibata: J.Org.Chem.51. 2177-2184 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Fujiwawa: Chem.Lett.1986. 1963-1966 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Baba: "Novel Use of Organotin Halide-Base Complex in Organic Synthesis; Cycloaddition Reaction of Oxetane with Isocyanates" Tetrahedron Lett.26. 5167-5170 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Baba: "Unusual Cycloaddition of Oxiranes with Isocyanates Catalyzed by Tetraphenylstibonium Iodide: Selective Formation of 3,4-Disubstituted Oxazolidinones" Tetrahedron Lett.27. 77-80 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I. Shibata: "Cycloaddition Reaction of Heterocumulenes with Oxiranes Catalyzed by Organotin Halide-Lewis Base Omplexes" J. Org. Chem.51. 2177-2184 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Fujiwara: "Cycloaddition Reaction of 2,3-Disubstituted Oxiranes with Isocyanates by Highly Activated Catalyst; Ph_4SbI-Bu_3SnI" Chem. Lett.1986. 1963-1966 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Baba: Tetrahedron Lett.26. 5167-5170 (1985)

    • Related Report
      1986 Annual Research Report
  • [Publications] A.Baba: Tetrahedron Lett.27. 77-80 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] I.Shibata: J.Org.Chem.51. 2177-2184 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Fujiwara: Chem.Lett.1986. 1963-1966 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Tetrahedron Letters. 26巻-42号. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron Letters. 27巻-1号. (1986)

    • Related Report
      1985 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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