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Synthetic Study of [0^4] Paracyclophane Using Valence-Bond Isomerization of Dewar Benzenes

Research Project

Project/Area Number 07640698
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

OHKITA Masakazu  Hokkaido University, Graduate School of Science, Instructor, 大学院・理学研究科, 助手 (60211786)

Co-Investigator(Kenkyū-buntansha) TSUJI Takashi  Hokkaido University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (20029482)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1995: ¥900,000 (Direct Cost: ¥900,000)
KeywordsDewar benzene / Cyclophanes / [0^n] Paracyclophane / Belt-type molecules / 〔O^4〕パラシクロファン
Research Abstract

In the present study, a novel belt-type molecule, [0^4] paracyclophane 1, composed of bent benzene rings was designed and attempted to be synthesized by using valence-bond isomerization of Dewar benzenes in the final step.
In 1996,8,10-dichloro-3,5-dioxobicyclo [5.2.2] undeca-8,10-diene 2 was synthesized in four steps from dimethyl acetylenedicarboxylate as a new Dewar benzene building block and its molecular structure and chemical reactivity were examined.
In 1997, synthesis of butadiene-expanded [0^6] paracyclophane 3 from the building block 2 was examined and the corresponding oligo (Dewar) benzene precursor was successfully synthesized. Model compound for 3, in which four paraphenylene units in 3 are replaced by metaphenylene units, was also synthesized.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Masakazu Ohkita: "Reaction of C_<60> with Cyclopent-2-enone Aceals. A Convenient Access to Chiral C_<60> Derivatives" J. Chem. Soc., Chem. Commun.1769-1770 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: "Direct Synthesis of 2-Norbornanone Dithioacetals from 20-Cyclopentenone Dithioacetals and Dienophiles. Synthetic Application of Thermal Interconversion between Cyclic Dithioacetals and the Ring-Opened Vinyl Sulfide Forms" Tetrahedron. 52. 9979-9990 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: "The Chemistry of the Cyclopropyl Group, Vol. 2" Ed by Z. Rappoport, John Wiley, New York,962 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: "Direct Synthesis of 2-Norbornanone Dithioacetals from 2-Cyclopentenone Dithioacetals and Dienophiles. Synthetic Application of Thermal Interconversion between Cyclic Dithioacetals and the Ring-Opened Vinyl Sulfide Forms" Tetrahedron. Vol.52. 9979-9990 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: "Reaction of C_<60> with Cyclopent-2-enone Acetals. A Convenient Access to Chiral C_<60> Derivertives" J.Chem.Soc., Chem.Commum.1769-1770 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: The Chemistry of the Cyclopropyl Group, Vol.2. Ed by Z.Rappoport, John Wiley, New York, 962 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masakazu Ohkita: "Direct Synthesis of 2-Norbornanone Dithioacetals from 2-Cyclopentenone Dithioacetals and Dienophils. Synthetic Application of Thernal Interconversion between Cyclic Dithioacetals and RIng-Opened Vinyl Sulfide Forms" Tetrahedron. 52. 9979-9990 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masakazu Ohkita: "Reaction of C_<60> with Cyclopent-2-enone Acetals.A Convenient Access to Chiral C_<60> Derivatives" J.Chem.Soc,Chem.Commun.1769-1770 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masakazu Ohkita: "The Chemistry of the Cyclopropyl Group,Vol.2" Ed by Z.Rappoport,John Wiley,New York,962 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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