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1996 Fiscal Year Final Research Report Summary

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
Keywordssigma-pi conjugation / C-C hyperconjugation / bicyclo [2.2.2] octene / silole / germole / cation radical / benzyne / anthracene
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.

  • Research Products

    (15 results)

All Other

All Publications (15 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-03-16  

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