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Synthesis of Functionalized Norcaradiene Derivatives

Research Project

Project/Area Number 06640679
Research Category

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

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionCHIBA UNIVERSITY

Principal Investigator

KOHMOTO Shigeo  Chiba University, Department of Materials Science, Associate Professor, 工学部, 助教授 (90195686)

Co-Investigator(Kenkyū-buntansha) KISHIKAWA Keiki  Chiba University, Department of Materials Science, Assistant Professor, 工学部, 助手 (40241939)
YAMAMOTO Makoto  Chiba University, Department of Materials Science, Pofessor, 工学部, 教授 (50039294)
YAMADA Kazutoshi  Chiba University, Department of Materials Science, Pofessor, 工学部, 教授 (60009230)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1995: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1994: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsNorcaradiene / Valence isomerization / Conformation control / Solvatochromic / Cyclopropene / Hydrogen transferred photorearrangement / Aromatization / 光[2+2]環化付加反応 / コンフォメーション制御 / バレンス異性化 / 光[2+2]環化反応 / スピロラクトン
Research Abstract

Utilization of norcaradiene-cycloheptatriene valence isomerization, one of the most typical valence isomerization, was attempted for a development of new functinalized materials.
(1) Attempt to develop a new solvatochromic system ; Control of norcaradiene-cycloheptatriene valence isomerization has been accomplished in 1,7-lactone and 1,7-lactam ring fused norcaradienes by protonation. Remarkable carbon chemical shift change was observed.
(2) Conformational control of 1,7-lactol ring fused norcaradienes ; Using intramolecular hydrogen bonding, the restricted rotation occurring in the norcaradiene system was locked. This locking was unlocked by the solvation with alcohol or dimethyl sulfoxide.
(3) Selective cleavage of cyclopropane sigma-bond of norcaradiene ; The C_1-C_7 bond of 1,7-lactol ring fused norcaradienes was selectively and conveniently cleaved to result in the dehydrative aromatization.
(4) Mechanism of the hydrogen transferred photorearrangement ; In order to elucidate the mechanism of the hydrogen transferred photorearrangement often reported in the photo [2+2] cycloaddition, photochemistry of cyclopropene derivatives (synthetic intermediate for norcaradienes) was investigated. It was found that steric factors controlled the course of photoreaction whether a [2+2] cycloaddition or a hydrogen transferred rearrangement.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Shigeo KOHMOTO: "Conformation of N-cyclopropylcarbonylureas. Solvent polarity dependent chemical shifts." J.Chem.Soc., Perkin Trans.2. 1565-1568 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo KHOMOTO: "Acid catalyzed dehydrative Aromatization of 1,7-lactol ring fused and 7-hydroxymethyl norcaradienes : A specific cleavage of the C_1-C_7 bond." Tetrahedron Lett.36. 553-554 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo KOHMOTO: "Photochemical formal [4π+2π+2π] cycloreversion of 7,8-diaza-3-oxatricyclo [4.2.1.0^<2,5>] non-7-enes." J.Phys.Org.Chem.8. 899-904 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo KOHMOTO: "Conformation of acylureas. Solvent polarity dependent specific rotation and the formation of molecular complexes with solvent molecules possessing a carbonyl or epoxy functionality" J.Chem.Soc., Perkin Trans.2. (印刷中). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo KOHMOTO: "Conformation of 7-vinylnorcaradienes. Conformational locking by intramolecular hydrogen bonding and Its Unlocking by solvation." J.Chem.Soc., Perkin Trans.1. (投稿中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto, Hideaki Kashimura, Takehiko Nishio, Ikuo Iida, Makoto Yamamoto, and Kazutoshi Yamada: "Conformation of N-Cyclopropylcarbonylureas. Solvent Polarity Dependent Chemical Shifts." J.Chem. Soc., Perkin Trans.2. 1565-1568 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto, Ichiro Koyano, Takayuki Funabashi, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada: "Acid Catalyzed, Dehydrative Aromatization of 1,7-Lactol Ring Fused and 7-Hydroxymethyl Norcaradienes : A Specific Cleavage of the C_1-C_7 Bond." Tetrahedron Lett.36. 553-554 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada: "Photochemical Formal [4pi+2pi+2pi] Cycloreversion of 7,8-Diaza-3-oxatricyclo [4.2.1.0^<2,5>] non-7-enes." J.Phys. Org. Chem.8. 799-804 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto, Naoki Iwasaki, Daisuke Fukui, Takehiko Nishio, Ikuo Iida, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada: "Conformation of Acylureas. Solvent Polarity Dependent Specific Rotation and the Formation of Molecular Complexes with Solvent Molecules Possessing a Carbonyl or Epoxy Functionality." J.Chem. Soc., Perkin Trans.2(in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto, Ichiro Koyano, Teruyuki Kawatsuji, Hideaki Kashimura, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada: "Conformation of 7-Vinylnorcaradienes. Conformational Locking by Intramolecular Hydrogen Bonding and Its Unlocking by Solvation." J.Chem. Soc. Perkin Trans.1(submitted.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Shigeo Kohmoto: "Acid catalyzed dehydrative Aromatization of 1,7‐lactol ring fused and 7‐hydroxymethyl norcaradienes: A specific cleavage of the C_1‐C_7 bond." Tetrahedron Lett.36. 553-554 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Shigeo Kohmoto: "Photochemical formal [4π+2π+2π]cycloreversion of 7,8‐diaza‐3‐oxatricyclo[4.2.1.0^<2,5>]non‐7‐enes." J. Phys. Org. Chem.8. 899-904 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Shigeo Kohmoto: "Conformation of acylureas. Solvent polarity dependent specific rotation and the formation of molecular complexes with solvent molecules" J. Chem. Soc., Perkin Trans. 2. (印刷中). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Shigeo Kohmoto: "Acid Catalyzed Dehydrative Aromatization of 1,7-Lactol Ring Fused and 7-Hydroxymetheyl Norcaradienes:A Specific Cleavage of the C_1-C_7 bond." TetrahedronLetters. 36. 553-554 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Keiki Kishikawa: "Novel Three-Component Couping Reaction of Carbodiimide,Methyl Hydrogen Maleate,and an Alcohol or Aimine:Synthesis of N-Carbamoylaspartic Acid." Journal of Chemical Society,Perkin Trans.1. 1205-1209 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Keiki Kishikawa: "Stereoselective Synthesis of 2-Alkylamino-N-(2'-alkylphenyl)succinimide Conformers." Chemistry Letters. 1605-1606 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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