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Systematic Studies on the Synthesis, Structures, and Properties of Aromatic Compounds Containing Heavier Group 14 Elements

Research Project

Project/Area Number 11304045
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyoto University (2000-2001)
Kyushu University (1999)

Principal Investigator

TOKITOH Norihiro  Kyoto University, Institute for Chemical Research, Professor, 化学研究所, 教授 (90197864)

Co-Investigator(Kenkyū-buntansha) TAKEDA Nobuhiro  Kyoto University, Institute for Chemical Research, Instructor, 化学研究所, 助手 (80304731)
Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥38,510,000 (Direct Cost: ¥36,500,000、Indirect Cost: ¥2,010,000)
Fiscal Year 2001: ¥8,710,000 (Direct Cost: ¥6,700,000、Indirect Cost: ¥2,010,000)
Fiscal Year 2000: ¥7,800,000 (Direct Cost: ¥7,800,000)
Fiscal Year 1999: ¥22,000,000 (Direct Cost: ¥22,000,000)
Keywordssteric protection / kinetic stabilization / silbenzene / 1-silanaphthalene / 2-silanaphthalene / 9-silaanthracene / germabenzene / 2-germanaphthalene / 芳香族化合物 / ゲルマニウム
Research Abstract

There has been no stable, neutral heteraaromatic compounds containing heavier group 14 elements, and their structures and properties have been revealed yet. In this Project, we studied on the synthesis of new type of heteraaromatic compounds containing a heavier group 14 element by taking advantage of an effective steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), which is developed by us, and elucidated their structures and properties. Based on these results, we estimated the aromaticity of these compounds, systematically.
We succeeded in the synthesis and isolation of the first stable silabenzene, 1-silanaphthalene, 2-silanaphthalene, 9-silaanthracene, germabenzene, and 2-germanaphthalene as stable crystals by taking advantage of Tbt group. The X-ray structural analyses, spectral data on NMR, UV/vis, and Raman spectroscopy, and theoretical calculations indicated that all these compounds are aromatic compounds as aromaticity these compounds showed the high reactivities to H_2O, alcohols, olefins, alkynes, ketones, and nitrile oxides and underwent ready addition of these reagents to the Si=C or Ge=C double-bond.
We think that the new knowledge obtained in this project lays the foundations of the chemistry of heteraaromatic compounds containing heavier group 14 elements. We expect that novel properties and functions of heteraaromatic compounds containing heavier group 14 elements will be revealed on the basis of these results, showing the potential applicability and these chemistry will be applied to the synthesis of novel functional compounds and novel catalysis.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (72 results)

All Other

All Publications (72 results)

  • [Publications] Norihiro Tokitoh: "New Aspects in the Chemistry of Multiple-bonds to Heteroatoms"Pure & Appl. Chem.. 71. 495-502 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Generation and Reactions of an Overcrowded Diaryldilithiosilane"Chem. Lett.. 1999. 931-932 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "The Chemistry of Germanium-containing Heavy Ketones"Bull. Chem. Soc. Jpn.. 72. 1665-1684 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tsuyoshi Matsumoto: "The First Kinetically Stabilized Germanethiones and Germaneselones : Syntheses, Structures, and Reactivities"J. Am. Chem. Soc.. 121. 8811-8824 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Synthesis of Stable 2-Silanaphthalenes and Their Aromaticity"J. Am. Chem. Soc.. 121. 11336-11344 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Synthesis and Properties of an Overcrowded Silabenzene Stable at Ambient Temperature"Angew. Chem. Int. Ed.. 39. 634-636 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Ken Hatano: "The First Stable Heteracyclopropabenzene : Synthesis and Crystal Structure of a Silacyclopropabenzene"J. Am. Chem. Soc.. 122. 4829-4830 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Crystal Structure of a Stable Silabenzene and Its Photochemical Valence Isomerization into the Corresponding Silabenzvalene"J. Am. Chem. Soc.. 122. 5648-5649 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "A Novel Reaction Mode in the Cycloaddition of Thermally Generated Silylenes with Conjugated Dienes"Chem. Lett.. 2000. 622-623 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Separation of Orientational Disorder in the X-Ray Analysis of the Kinetically Stabilized 2-Silanaphthalene"Bull. Chem. Soc. Jpn.. 73. 2157-2158 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "New Aspects in the Chemistry of Low-coordinated Inter-element Compounds of Heavier Group 15 Elements"J. Organomet. Chem.. 611. 217-227 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Renji Okazaki: "Heavy Ketones, the Heavier Element Congeners of a Ketone"Acc. Chem. Res.. 33. 625-630 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Formation of Antimony-Sulfur Double-Bond Compounds and Their Trapping with Nitrile Oxides"Heteroatom Chem.. 12. 244-249 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Recent Advances in the Chemistry of Group 14-Group 16 Double Bond Compounds"Adv. Organomet. Chem.. 47. 121-166 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis, Structures, and Reactivities of Novel Silacyclic Systems : The First Stable Silabenzene and Silacyclopropabenzene"Phosphorus, Sulfur and Silicon. 168-169. 31-40 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Novel Disproporitionation Reaction of Stable Stibabismuthene via 1,2,3,4-Distibadibismetane Derivative"Phosphorus, Sulfur and Silicon. 168-169. 413-416 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "Reaction of Stable Silylene-Isocyanide Complexes with Boranes : Synthesis and Properties of the First Stable Silylborane-Isocyanide Complexes"Chem. Lett.. 2001. 1076-1077 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norio Nkata: "Synthesis and Structure of a Kinetically Stabilized 2-Germanaphthalene : the First Stable Neutral Germaaromatic Compound"Organometallics. 20. 5507-5509 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kasuto Nagata: "Syntheses and Crystal Structures of the First Disulfur and Diselenium Complexes of Platinum"Angew. Chem. Int. Ed.. 41. 136-138 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Synthesis and Structure of the First Stable Phosphabismuthene"Angew. Chem. Int. Ed.. 41. 139-141 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis of Kinetically Stabilized Silaneselone and Silanetellone"Chem. Lett.. 2002. 34-35 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "The First Stable 9-Silaanthracene"Organometallics. 21. 256-258 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis and Characterization of an Extremely Hindered Tetraaryl-substituted Digermene and Its Properties in the Solid State and in Solution"Polyhedron. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Syntheses, Structures and Properties of Kinetically Stabilized Distibenes and Dibismuthenes, Novel Doubly Bonded Systems between Heavier Group 15 Elements"Bull. Chem. Soc. Jpn. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Formation of Antimony-Sulfur Double-Bond Compounds and Their Trapping with Nitrile Oxides"Pure & Appl. Chem.. 71. 495-502 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] N. Tokitoh: "Generation and Reactions of an Over-crowded Diaryldilithiosilane"Chem. Lett.. 1999. 931-932 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Taketh: "The Chemistry of Germanium-containing Heavy Ketone"Bull. Chem. Soc. Jpn.. 72. 1665-1684 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tsuyoshi Matsumoto: "The First Kinetically Stabilized Germanethiones and Germaneselones : Syntheses, Structures, and Reactivities"J. Am. Chem. Soc.. 121. 8811-8824 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Synthesis of Stable 2-Silanaphthalenes and Their Aromaticity"J. Am. Chem. Soc.. 121. 11336-11344 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Synthesis and Properties of an Overcrowded Silabenzene Stable at Ambient Temperature"Angew. Chem. Int. Ed.. 39. 636-638 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Ken Hatano: "The First Stable Heteracyclopropabenzene : Synthesis and Crystal Structure of a Silacyclopropabenzene"J. Am. Chem. Soc.. 122. 4829-4830 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Crystal Structure of a Stable Silabenzene and Its Photochemical Valence Isomerization into the Corresponding Silabenzvalene"J. Am. Chem. Soc.. 122. 5648-5649 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "A Novel Reaction Mode in the Cycloaddition of Thermally Generated Silylenes with Conjugated Dienes"Chem. Lett.. 2000. 622-623 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keiji Wakita: "Separation of Orientational Disorder in the X-Ray Analysis of the Kinetically Stabilized 2-Silanaphthalene"Bull. Chem. Soc. Jpn.. 73. 2157-2158 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "New Aspects in the Chemistry of Low-coordinated Inter-element Compounds of Heavier Group 15 Element"J. Organomet. Chem.. 611. 217-227 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Renji Okazaki: "Heavy Ketones, the Heavier Element Congeners of a Ketone"Acc. Chem. Res.. 33. 625-630 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Formation of Antimony-Sulfur Double-Bond Compounds and Their Trapping with Nitrile Oxides"Heteroatom Chem.. 12. 244-249 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Recent Advances in the Chemistry of Group 14-Group 16 Double Bond Compounds"Adv. Organomet. Chem.. 47. 121-166 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis, Structures, and Reactivities of Novel Silacyclic Systems : the First Stable Silabenzene and Silacyclopropabenzene"Phosphorus, Sulfur and Silicon. 168-169. 31-40 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Novel Disproportionation Reaction of Stable Stibabismuthene via 1,2,3,4-Distibadibismetane Derivative"Phosphorus, Sulfur and Silicon. 168-169. 413-416 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "Reaction of Stable Silylene-Isocyanide Complexes Boranes : Synthesis and Properties of the First Stable Silylborane-Isocyanide Complexes"Chem. Lett.. 2001. 1076-1077 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norio Nakata: "Synthesis and Structure of a Kinetically Stabilized 2-Germanaphthalene : the First Stable Neutral Germaaromatic Compound"Organometallics. 20. 5507-5509 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kazuto Nagata: "Syntheses and Crystal Structures of the First Disulfur and Diselenium Complexes of Platinum"Angew. Chem. Int. Ed.. 41. 136-138 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Synthesis and Structure of the First Stable Phosphabismuthene"Angew. Chem. Int. Ed.. 41. 139-141 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis of Kinetically Stabilized Silaneselone and Silanetellone"Chem. Lett.. 2002. 34-35 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Nobuhiro Takeda: "The First Stable 9-Silaanthracene"Organometallics. 21. 256-258 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Synthesis and Characterization of an Extremely Hindered Tetraaryl-substituted Digermene and Its Unique State and in Solution"Polyhedron. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiro Sasamori: "Syntheses, Structures and Properties of Kinetically Stabilized Distibenes and Dibismuthenes, Novel Doubly Bonded Systems between Heavier Group 15 Elements"Bull. Chem. Soc. Jpn.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Norihiro Tokitoh: "Formation of Antimony-Sulfur Double-Bond Compounds and Their Their Trapping With Nitrile Oxides"Heteroatom Chem.. 12. 244-249 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Recent Advances in the Chemistry of Group 14-Group l6 Double Bond Compounds"Adv.Organomet.Chem.. 47. 121-166 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Synthesis, Structures, and Reactivities of Novel Silacyclic Systems : the First Stable Silabenzene and Silacyclopropabenzene"Phosphorus, Sulfur and Silicon. 168-169. 31-40 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Takahiro Sasamori: "Novel Disproportionation Reaction of Stable Stibabismuthene via 1, 2, 3, 4-Distibadibismetane Derivative"Phosphorus, Sulfur and Silicon. 168-169. 413-416 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Nobuhiro Takeda: "Reaction of Stable Silylene-Isocyanide Complexes with Boranes : Synthesis and Prop of the First Stable Silylborane-Isocyanide Conplexes"Chem.Lett.. 2001. 1076-1077 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Norio Nakata: "Synthesis and Structure of a Kinetically Stabilized 2-Germanaphthalene : the First Stable Neutral Germaaromatic Compound"Organometallics. 20. 5507-5509 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Kazuto Nagata: "Syntheses and Crystal Structures of the First Disulfur and Diselenium Complexes of Platinum"Angew.Chem.Int.Ed.. 41. 136-138 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Takahiro Sasamori: "syntheses, structures and Properties of Kinetically Stabilized Distibenes and Dibismuthenes, Novel Doubly Bonded SyStems between Heavier Group 15 Elements"Angew.Chem.Int.Ed.. 41. 139-141 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Synthesis of Kinctically Stabilized Silaneselone and Silanetellone"Chem.Lett.. 2002. 34-35 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Nobuhiro Takeda: "The First Stable 9-Silaanthracene"Organometallics. 21. 256-258 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Synthesis and Characterization of an Extremely Hindered Tetraaryl-substituted Dige and Its Unique Properties in the Solid State and in Solution"Polyhedron. (印刷中).

    • Related Report
      2001 Annual Research Report
  • [Publications] Takahiro Sasamori: "Syntheses, Structures and Properties of Kinetically Stabilized Distibenes and Dibismuthenes, Novel Doubly Bonded Systems between Heavier Group 15 Elements"Bull.Chem.Soc.Jpn.. (印刷中).

    • Related Report
      2001 Annual Research Report
  • [Publications] Ken Hatano: "The First Stable Heteracyclopropabenzene : Synthesis and Crystal Structure of a Silacyclopropabenzene"J.Am.Chem.Soc.. 122. 4829-4830 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Keiji Wakita: "Crystal Structure of a Stable Silabenzene and Its Photochemical Valence Isomerization into the Corresponding Silabenzvalene"J.Am.Chem.Soc.. 122. 5648-5649 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Nobuhiro Takeda: "A Novel Reaction Mode in the Cycloaddition of Thermally Generated Silylenes with Conjugated Dienes"Chem.Lett.. 2000. 622-623 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Keiji Wakita: "Separation of Orientational Disorder in the X-Ray Analysis of the Kinetically Stabilized 2-Silanaphthalene"Bull.Chem.Soc.Jpn.. 73. 2157-2158 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Recent Topics in the Chemistry of Heavier Congeners of Carbenes"Coord.Chem.Rev.. 210. 251-277 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Renji Okazaki: "Heavy Ketones, the Heavier Element Congeners of a Ketone"Acc.Chem.Res.. 2000. 625-630 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Norihiro Tokitoh: "New Aspects in the Chemistry of Multiple-bonds to heteroatoms"Pure&Appl.Chem.. 71. 495-502 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Norihiro Tokitoh: "Generation and Reactions of an Overowded Diaryldilithiosilane"Chem,Lett,. 1999. 931-932 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Norihiro Tokitoh: "The Chemistry of Germanium-containing Heavy Ketones"Bull,Chem,Soc,Jpn,. 72. 1665-1684 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tsuyoshi Matsumoto: "The First Kinetically Stabilized Germanethiones and Germaneselones ; Syntheses,Structures,and Reactivities"J,Am,Chem,Soc,. 121. 8811-8824 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Keiji Wakita: "Synthesis of Stable 2-Silanaphthalenes and Their Aromaticity"J,Am,Chem.Soc,. 121. 11336-11344 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Keiji Wakita: "Synthesis and Properties of an Overcrowded Silabenzene at Ambient Temperature"Angew,Chem,Int,Ed,. 39. 634-636 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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