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1994 Fiscal Year Final Research Report Summary

Synthesis and Properties of New Macrocyclic Conjugated Compounds

Research Project

Project/Area Number 05453029
Research Category

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

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionToyama University

Principal Investigator

OJIMA Juro  Department of Chemistry, Faculty of Science Toyama University Professor, 理学部, 教授 (00018988)

Co-Investigator(Kenkyū-buntansha) HIGUCHI Hiroyuki  Department of Chemistry, Faculty of Science Toyama University Associate Professo, 理学部, 助教授 (00165094)
Project Period (FY) 1993 – 1994
KeywordsNonbenzenoid Aromatics / Annulenedione / Ring Current Effect / Macrocycles / Conjugation
Research Abstract

Several new systems of macrocyclic conjugated compounds have been synthesized and their properties were examined.
In compounds (1) and (2) several annulenediones showed ring current effect under acidic conditions. Compounds (3) showed diatropicity under both neutral and acidic conditions, and their diatropicities proved to increase with increasing ring size.
In compound (4), the fused azulene ring reduecd the diatropicity of the 14pi-electron annulene of compound (4), but did not reduce the paratropicity of the 16pi-electron annulene of compound (5).

  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Hiroyuki Higuchi: "Annelated Dehydroannulenes Fused with Azulene Ring.The Synthesie of Bisdehydro[14]-and-[16]annuleno[a]azulene" Tetrahedron Lett.35. 1259-1262 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of a Bisdehydro[14]annuleno[c]furan and an Ortho-Annelated Tetrakisdehydro[14]annuleno[14]annulene" Bull.Chem.Soc.Jpn.67. 778-791 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Annelated Dehydroannulenes Fused with Azulene.Synthesis and Properties of Tetradehydro[14]-and-[16]annuleno[a]azulenes" J.Chem.Soc.,Perkin Trans.I. 1167-1177 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Formation of a Paratropic,Dicationic 24π-Electron System in D_2SO_4" J.Chem.Soc.,Chem.Commun.877-878 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Syntheses and Properties of Methano Bridged Dichlorodidehydro-[16]-,-[20]-and-[24]annulenediones" J.Chem.Soc.,Perkin Trans.I. 1453-1468 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Methano-bridged Tetradehydro[22]annulenedione21GC06:J.Chem.Soc.,Perkin Trans.I" 1579-1587 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Tetramethyloctadehydro-[26]-,-[28]-,-[30]-,-[32]-and-[34]annulenediones" J.Chem.Soc.,Perkin Trans.I. 1957-1968 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Unusual Formation of Tricyclic Annulenediones.Diatropic Cationic 10π-Electron Species in D_2SO_4" J.Chem.Soc.,Perkin Trans.I. 2915-2920 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Gaku Yamamoto: "Stereodynamics of N-Benzyl-N-methyl-9-aminotriptycene" Chem.Lett.1911-1914 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of a Bismethano-bridged Bisdehydro[21]-annulenone.Conformation in Solution and in the Crystalline State" Chem.Lett.2291-2294 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Higuchi: "Annelated Dehydroannulenes Fused with Azulene Ring. The Synthesis of Bisdehydro [14] - and - [16] annuleno [a] azulene" Tetrahedron Lett.35. 1259-1262 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of a Bisdehydro [14] annuleno [c] furan and an Ortho-Annelated Tetrakisdehydro [14] annuleno [14] annulene" Bull.Chem.Soc.Jpn.67. 778-791 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Annelated Dehydroannulenes Fused with Azulene. Synthesis and Properties of Tetradehydro [14] - and - [16] annuleno [a] azulenes" J.Chem.Soc., Perkin Trans.I. 1167-1177 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Formation of a Paratropic, Dicationic 24pi-Electron System in D_2SO_4" J.Chem.Soc., Chem.Commun.877-878 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Syntheses and Properties of Methano Bridged Dichlorodidehydro- [16] -, - [20] - and - [24] annulenediones" J.Chem.Soc., Perkin Trans.I. 1453-1468 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Methano-bridged Tetradehydro [22] - annulenedione" J.Chem.Soc., Perkin Trans.I. 1579-1587 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Tetramethyloctadehydro- [26] -, - [28] -, - [30] -, - [32] - and - [34] annulenediones" J.Chem.Soc., Perkin Trans.I. 1957-1968 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Unusual Formation of Tricyclic Annulenediones. Diatropic Cationic 10pi-Electron Species in D_2SO_4" J.Chem.Soc., Perkin Trans.I. 2915-2920 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Gaku Yamamoto: "Stereodynamics of N-Benzyl-N-methyl-9-aminotriptycene" Chem.Lett.1911-1914 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of a Bismethano-bridged Bisdehydro - [21] annulenone. Conformation in Solution and in the Crystalline State" Chem.Lett.2291-2294 (1994)

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

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Published: 1996-04-15  

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