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Synthesis and Properties of Novel pi-Electronic Hydrocarbons Having sigma-pi Interaction

Research Project

Project/Area Number 07454165
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

KOMATSU Koichi  Kyoto University, Institute for Chemical Research, Professor, 化学研究所, 教授 (70026243)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥6,300,000 (Direct Cost: ¥6,300,000)
Fiscal Year 1996: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1995: ¥5,000,000 (Direct Cost: ¥5,000,000)
Keywordssigma-pi conjugation / C-C hyperconjugation / bicyclo [2.2.2] octene / silole / germole / cation radical / benzyne / anthracene / σ-π共役 / ビシクロオクテン / デヒドロアヌレン / カップリング 反応 / サイクリック ボルタメトリー / σ-π相互作用 / π共役素 / 酸化還元 / バンザイン
Research Abstract

1.Synthesis of the Cyclopentadienylpi-System Annelated with Bicyclooctene Frameworks.
Bicyclo [2.2.2] octene (abbreviated as BCO) was used as the structural unit for the synthesis of pi-systems having novel properties. Thus, a series of substituted cyclopentadienyl derivatives annelated with two BCO units have been synthesized and their redox behaviors investigated in detail.
2.Synthesis of Sila-and Germacyclopentadienes Annelated with BCO Units.
The above silole and germole derivatives have been newly synthesized and their spectral properties fully characterized. The presence of sigma-pi interaction has been investigated based on the results of UV data and MO calculations.
3.Generation of the Benzyne Annelated with Two BCO Units.
The generation of the above mentioned benzyne has been confirmed by trapping experiment. This benzyne has also been converted to the biphenylene derivative and its unique redox behaviors were clarified.
4.Synthesis and Properties of the Anthracene Annelated with Four BCO Units.
The above mentioned anthracene derivative has been newly synthesized by the use of double Diels- Alder reaction of the BCO dimer with p-benzoquinone as a dienophile. The notable increase in HOMO level owing to the sigma-pi interaction has been demonstrated by the use of electrochemical and organochemical redox reactions. The stable cation radical and dication have successfully been generated from this anthracene derivative.

Report

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

    (26 results)

All Other

All Publications (26 results)

  • [Publications] 小松 紘一: "剛直なσ炭素骨格で囲まれたπ共役系環状炭化水素の合成と性質 ◇ C-C超共役の効果" 有機合成化学協会誌. Vol.54, No.10. 868-878 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 西長 亨、小松 紘一: "σ-π共役、C-C超共役" 有機合成化学協会誌. Vol.54, No.10. 876-879 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N.kaneta, K.Komatsu et al.: "Electronic Interaction of Tricarbon ylchromium-Complexed Benzene with a Facing Aryl Ring in the 1, 8-Diarylnapha thalene System" Tetrahedron Letters. Vol.37, No.30. 5385-5388 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nishinaga, K.Komatsu et al.: "Synthesis and Properties of Dehydroannulenes Annelated with Bicyclo[2.2.2]octene Framewroks" Journal of Organic Chemistry. (発表予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Matsuura, K.Komatsu et al.: "Synthesis and Properties of Novel Anthracene Tetra-annelated with Bicyclo[2.2.2]octene Frameworks" Tetrahedron Letters. (発表予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Kudo, K.Komatsu et al.: "Hydrocarbonylation of Enol Esters Catalyzed by a Palladium(II)Complex" Bull.Chem.Soc.Jpn.Vol.69, No.5. 1337-1345 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Komatsu, Z.Yoshida: "Houben-Weyl, Methods of Organic Chemistry, "Cycloprop enylium Salts"" Georg Thieme Verlag, Stuttgart, 115 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Komatsu: "Synthesis and Properties of Cyclic pi-Conjugated Hydrocarbons Surrounded by Rigid sigma-Frameworks ---- the Effects of C-C hyperconjugation" J Synth.Org.Chem.Jan.vol.54, No.10. 868-878 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nishinaga: "sigma-pi conjugation, C-C Hyperconjugation" J Synth.Org.Chem.Jpn.vol.54, No.10. 879-879 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N.Kaneta: "Electronic Interaction of Tricarbonylchromium-Complexed Benzene with a Facing Aryl Ring in the 1,8-Diarylnaphthalene System" Tetrahedron Lett.vol.37, No.30. 5385-5388 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nishinaga: "Synthesis and Properties of Dehydroannulenes Annelated with Bicyclo [2.2.2] octene Frameworks" J.Org.Chem.(submitted for publication).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Matsuura: "Synthesis and Properties of Novel Anthracene Tetra-annelated with Bicyclo [2.2.2] octene Frameworks" Tetrahedron Lett.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Matsuura: "Reactions of a Novel Benzyne Annelated with Two Bicyclo [2.2.2] octene Units" Tetrahedron Lett.(submitted for publication).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Kudo: " Hydrocarbonylation of Enol Esters Catalyzed by a Palladium (II) Complex" Bull.Chem.Soc.Jpn.vol.69, No.5. 1337-1345 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Komatsu: Houben-Weyl, Methods of Organic Chemistry, Cyclopropenylium Salts. Georg Thieme Verlag, stuttgart., 3079-3193 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 小松紘一: "剛直なσ炭素骨格で囲まれたπ共役系環状炭化水素の合成と性質-C-C超共役の効果" 有機合成化学協会誌. vol.54. 868-878 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 西長亨、小松紘一: "σ-π共役、C-C超共役" 有機合成化学協会誌. vol.54. 876-879 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N.Kaneta,K.Komatsu et al.: "Electronic Interactionof Tricarbonnyichromium-Complexed Benzene with a Facing Aryl Ring in the 1,8-Diary Inapahthalene System" Tetrahedron Letters. vol.37. 5385-5388 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Nishinaga,K.Komatsu et al.: "Synthesis and propertis of Dehydroannulenes Annelated with Bicyclo[2.2.2]octene Framewroks" Jouanal of Organic Chemistry. (発表予定).

    • Related Report
      1996 Annual Research Report
  • [Publications] A.Matsumura,K.Komatsu et al.: "Synthesis and propertis of Novel Anthracene Tetra-annelated with Bicyclo[2.2.2]octene Framewroks" Tetrahedron Letters. (発表予定).

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Kudo,K.Komatsu et al.: "Hydrocarbonylation of Enol Esters Catalyzed by a Palladium (II) Complex" Bull.Chem.Soc.Jpn.vol.69. 1337-1345 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Komatsu,Z.Yoshida: "Houben-Weyl,Methods of Organic Chemistry,"Cycloproprenylium Salts"" Georg Thieme Verlag,Stuttgart, 115 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tohru Nishinaga: "1, 1-Dimethylsila-, -germa-, and -stannacycloheptatrienes Fully Annelated with Bicyclooctene: Synthesis, Structures, and Properties" Journal of Organic Chemistry. 60. 1309-1314 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Sadayuki Mori: "Carbonylation of Trichloroacetaldehyde in Conc. Sulfuric Acid: Stereocontrolled Synthesis of cis-&trans-2, 5-Bis(trichloromethyl)-1, 3-dioxolan-4-ones" Tetrahedron. 51. 8977-8982 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Yasushi Ohga: "Chain Carbonylation of Methoxymethyl Chloride by Using AgSbF_6 Catalyst under High Pressure of CO" Tetrahedron. 51. 11119-11124 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kiyoshi Kudo: "Novel Synthesis of Oxalate from Carbon Dioxide and Carbon Monoxide in the Presence of Cesium Carbonate" Journal of Chemical Society, Chemical Communications. 633-634 (1995)

    • Related Report
      1995 Annual Research Report

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

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