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New Synthetic Approaches to the Seven-Membered Oxocarbon

Research Project

Project/Area Number 60470025
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKyushu University

Principal Investigator

MORI Akira  Institute of Advanced Material Study, Associate Professor, 機能物質科学研究所, 助教授 (70038602)

Project Period (FY) 1985 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥5,500,000 (Direct Cost: ¥5,500,000)
Fiscal Year 1987: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1986: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1985: ¥4,000,000 (Direct Cost: ¥4,000,000)
KeywordsOxocarbon / Oxidation-Reduction Potentials of p-Tropoquinones / Solvolysis / Acetotropy / [1,9]Sigmatropy / トロポノイドの陽極酸化 / 加溶媒分解反応 / 〔1,9〕-シグマトロピー
Research Abstract

Monocyclic oxocarbon dianions C_nO_n^<2-> ( n=3-6 ) have been expressed to be symmetric D_<nh> structures from the results of a study of vibrational spectra. The higher homologue C_7O_7^<2->, however, is an unknown species. The main purpose in this research project was the synthesis of C_7O_7^<2-> species and intensive efforts were focussed on 1) introductions of oxygenated functional groups to the seven-membered ring and 2) their effective oxidations to polyketonic species.
In the process, although the synthesis of C_7O_7^<2-> species has not succeeded yet, following intriguing results were disclosed; they were a) preparations of polyacetoxy- and polyhydroxytropones by solvolytic reaction conditions, b) mechanistic evidences for an acetotropy in 2-acetoxytropones, c) an estimation of oxidation potentials of functionalyzed p-tropoquinones, d) preparations of tropoquinone acetals by anodic oxidations, and e) the conformational analysis and photorearrangements of 4,4,5,5-tetramethoxycyclohepta-2,6-dienones.

Report

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

    (46 results)

All Other

All Publications (46 results)

  • [Publications] Akira Mori: Chemistry Letters. 155-156 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.59. 511-514 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Chemistry Letters. 593-596 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Bull. Chem. Soc. Jpn.59. 1125-1128 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Synthesis. 578-579 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Kyushu Daigaku Chuoubunseki Center Hokoku. 62-66 (4)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Bull. Chem. Soc. Jpn.60. 1429-1432 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Bull. Chem. Soc. Jpn.60. 1747-1752 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.60. 2497-2501 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.60. 3037-3038 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Chemistry Letters. 1931-1934 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.60. 3817-3819 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Bull. Chem. Soc. Jpn.60. 4235-4333 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Bull. Chem. Soc. Jpn.60. 4335-4338 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.60. 4339-4341 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Chemistry Letters. 71-72 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Chemistry Letters. 175-178 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Kyushu Daigaku Kinobussitsu Kagaku Kenkyusho Hokoku. 1. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: Kyushu Daigaku Kinobussitsu Kagaku Kenkyusho Hokoku. 1. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: Bull. Chem. Soc. Jpn.61. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Cyclic Voltammetry of p-Tropoquinones" Chemistry Letters. 155-156 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "The Cerium(IV) Ammonium Nitrate Oxidation of 5-Hydroxy-2-methoxytropone to Bitropolonyl Derivatives and One-step Synthesis of 3-Methoxy-p-tropoquinone" Bull. Chem Soc. Jpn.59. 511-514 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "An Anion-promoted Rearrangement of 2-(0- and p-Nitrobenzyloxy)tropones to a-Hydroxylated 2-(0- and p-Nitrobenzyl)tropones. A Ready Introduction of Aralkyl Group into the Troponoid Nucleus" Chemistry Letters. 593-596 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "Synthesis of 3-Arylmethyl-p-tropoquinones from 5-Alkoxy-2-(arylmethoxy)tropones via Homolytic Rearrangement and Oxidation" Bull. Chem. Soc. Jpn.59. 1125-1128 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "An Improved Synthesis of 2,7-Dihydroxytropone (3-Hydroxytropolone)" Synthesis. 578-579 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira mori: "Kinetic Study for Degenerated Acetotropy of Hexaacetoxytropone by Means of High- Resolution NMR (in Japanese)" Kyushu Daigaku Chuoubunseki Center Hokoku. 4. 62-66 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "A Novel Base-promoted Rearrangement of 2-(4-Cyano, 2-Nitro, and 4-Nitrobenzyloxy)tropones to 2-(4-Cyano, 2-Nitro, and 4-Nitrophenyl)hydroxymethyltropones" Bull. Chem. Soc. Jpn.60. 1429-1432 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "Thermal Rearrangement of 2,5-Bis(allyloxy)tropone, Revisited. Formation of Four Thermolysates under the Claisen Rearrangement Conditions and Structure Revision of the Major Thermolysate" Bull. Chem. Soc. Jpn.60. 1747-1752 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Synthesis and Electrochemical Properties of 3-(3,6-Dioxo-1,4-cyclohexadienyl)methyl-p- Tropoquinone. Analysis of a Four-electron Redox System by Cyclic Voltammetry" Bull. Chem. Soc. Jpn.60. 2497-2501 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Synthetic Photochemistry. XXXVIII. The Photorearrangement of the Tropone Endoperoxide, 6,7-Dioxabicyclo[3.2.2]nona-3,8-dien-2-one" Bull. Chem. Soc. Jpn.60. 3037-3038 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Direct Formations of o-Tropoquinone Bisacetals from 2,3- and 2,7-Dimethoxytropones and p-Tropoquinone Bisacetals from 2-Bromo-7-methoxytropone by the Anodic Oxidation" Bhemistry Letters. 1931-1934 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Synthetic Photochemistry. XXXiX. Sensitized-Photooxygenation of 2-Benzyltropone, 2-[Hydroxy(4-nitrophenyl)methyl]tropone, and 2-(1-Hydroxy-2-oxo-2-phenylethly)tropone. A Quenching Effect of Hydroxyl Group in the Vicinity of the Reaction Site" Bull. Chem. Soc. Jpn.60. 3817-3819 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "Preparation of Polyacetoxytropones and Polyhydroxytropolones by Acetolysis and Hydrolysis of Halotroponoids by Acetyl Trifluoroacetate with Exhaustive Displacement of Halogens on the Tropone Ring. Predominant Formation of Reductive Acetolysates from Fully-Substituted Tropones" Bull. Chem. Soc. Jpn.60. 4325-4333 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "The Kinetic Evidence of the Concerted [1,9]Sigmatropy for the Acetyl Migration in the 2-Acetoxytropones. The NMR Spectral Analysis of the Seven-Fold Degenerated Acetotropy of Hexaacetoxytropone" Bull. Chem. Soc. Jpn.60. 4335-4338 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "The Solid-Phase ^<13>C NMR Spectra of Several Tropolone Derivatives" Bull. Chem. Soc. Jpn,. 60. 4339-4341 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Photorearrangement of 4,4,5,5-Tetramethoxycyclohepta-2,6-dienones to 6,6,7,7-Tetra- methoxybicyclo[3.2.0]hept-3-en-2-ones" Chemistry Letters. 71-72 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "Spectral Evidence for the J-Aggregate Formation of a Non-Benzenoid Aromatic Dye, Dicyclohepta[[5,6:b]]pyrazino[[2,3-g]]quinoxaline-3,11-dione" Chemistry Letters. 175-178 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "Synthesis of Bis(2,6-dihydroxy-5-oxo-1,3,6-cycloheptatrienyl)methane from 2-Alkoxy- 5-hydroxytropones and the Electrochemical Properties of Bis(3,4,7-trioxo-1,5-cyclo- heptadienyl)methane Derivatives" Kyushu Daigaku Kinobussitsu Kagaku Kenkyusho Hokoku. 1. in press (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hitoshi Takeshita: "Synthesis of 4,6-Dicyano-2,5-dimethoxytropone" Kyushu Daigaku Kinobussitsu Kagaku Kenkyusho Hokoku. 1. in press (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Akira Mori: "The Cyclic Voltammetry of p-Tropoquinone Acetals" Bull. Chem. Soc. Jpn.61. in press (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Mori;T.Kusaba;Y.Isayama;H.Takeshita: Chemistry Letters. 155-156 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] A.Mori;Y.Isayama;H.Takeshita: Bulletin of the Chemical Society of Japan. 59. 511-514 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Takeshita;A.Mori;H.Suizu: Chemistry Letters. 593-596 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Takeshita;A.Mori;Y.Goto: Bulletin of the Chemical Society of Japan. 59. 1125-1128 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Takeshita;A.Mori;H.Suizu: Bullctin of the Chemical Society of Japan. 60. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] A.Mori;Y.Goto;H.Takeshita: Bulletin of the Chemical Society of Japan. 60. (1987)

    • Related Report
      1986 Annual Research Report

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

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