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2006 Fiscal Year Final Research Report Summary

Research on the Synthesis, Structure, and Reactivity of Aromatic Compound Consisting of Heavier Main Group Elements

Research Project

Project/Area Number 16550028
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionUniversity of Tsukuba

Principal Investigator

ICHINOHE Masaaki  University of Tsukuba, Graduate School of Pure and Applied Sciences, Associate Professor, 大学院数理物質科学研究科, 助教授 (90271858)

Project Period (FY) 2004 – 2006
KeywordsMain Group Element Chemistry / Heavier Main Group Element / Structural Organic Chemistry / Aromatic Compound
Research Abstract

Aromatic hydorocarbons such as benzene and naphthalene, are fundamental group of organic compounds, and also plays important roles in organic chemistry. In contrast, the chemistry of stable metallaaromatic compounds such as sila- and germa- aromatic systems, in which skeletal atom(s) are partially replaced by heavier Group 14 elements, is new, and have been recently developed. In this project, we investigated the chemistry of stable aromatic compounds consisting of heavier group 14 elements ; the development of synthetic methods, analysis of structure, property, and reactivity of them.
We succeeded in synthesize and characterize cyclotrisilenylium ion by the oxidative desilylation reaction of cyclotrisilene bearing extremely bulky triorganosilyl groups. Cyclotrisileniylium ion has near regular triangle three membered ring indicating its aromatic character in analogy with cyclopropenylium ion with 2π aromatic system. On the other hand, dipotassium salt of tetrasilacyclobutadiene dianion as heavier analogue of cyclobutadiene dianion with 6π aromatic system synthesized by the reductive debromination and additional two-electron reduction of 1,2,3,4-tetrabromocyclotetrasilane, has large bent four membered ring coordinated by two potassium cations up and below, and we concluded that heavier cyclobutadiene dianion is non-aromatic by the reason why planer three-coordinate geometry is not preferred in negatively charged organosilicon compounds. Additionally, we also succeeded in the synthesis of disilagermacyclopentadienide ion as 6π electron aromatic compound.

  • Research Products

    (48 results)

All 2007 2006 2005 2004

All Journal Article (48 results)

  • [Journal Article] An Isolable Disilyne Anion Radical and a New Route to the Disilenide Ion upon Reduction of a Disilyne2007

    • Author(s)
      Rei Kinjo
    • Journal Title

      Journal of the American Chemical Society 129・1

      Pages: 26-27

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Heavy Cyclopropene Analogues R_4SiGe_2 and R_4Ge_3(R = SiMe^tBu_2) New Members of the Cyclic Digermenes Family2007

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Journal of Organometallic Chemistry 692・1-3

      Pages: 10-19

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Conversion of Disilenide into Silene : Silyl Anion-substituted Silene by a Sila-Peterson-type Reaction from an sp^2-type Silyl Anion2007

    • Author(s)
      Shigeyoshi Inoue
    • Journal Title

      Angewandte Chemie, International Edition 46(印刷中)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Stable Cyclic Silenes from Reaction of Disinides with Carboxylic Acid Chlorides2007

    • Author(s)
      Iulia Bejan
    • Journal Title

      Angewandte Chemie, International Edition 46(印刷中)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Heavy Analogues of the 6π-Electron Anionic Ring Systems : Cyclopentadienide Ion and Cyclobutadiene Dianion2007

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Journal of Organometallic Chemistry (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] An Isolable Disilyne Anion Radical and a New Route to the Disilenide Ion upon Reduction of a Disilyne.2007

    • Author(s)
      R.Kinjo, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 26-27

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Heavy Cyclopropene Analogues R_4SiGe_2 and R_4Ge_3 (R=SiMe^tBu_2) New Members of the Cyclic Digermenes Family.2007

    • Author(s)
      V.Ya.Lee, H.Yasuda, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of Organometallic Chemistry 692

      Pages: 10-19

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Heavy Analogues of the 6π-Electron Anionic Ring Systems : Cyclopentadienide Ion and Cyclobutadiene Dianion.2007

    • Author(s)
      V.Ya.Lee, K.Takanashi, R.Kato, T.Matsuno, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of Organometallic Chemistry (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A (Tetrasilacyclobutadiene)tricarbonyliron complex [η^4-(^tBu_2MeSi)_4Si_4]Fe(CO)_3 : The Silicon Cousin of Pettit (Cyclobutadiene)tricarbonyliron complex (η^4-H_4C_4)Fe(CO)_32006

    • Author(s)
      Kazunori Takanashi
    • Journal Title

      Angewandte Chemie, International Edition 45・20

      Pages: 3269-3272

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The Chemistry of Disilyne with a Genuine Si-Si Triple Bond : Synthesis, Structure, and Reactivity2006

    • Author(s)
      Akira Sekiguchi
    • Journal Title

      Bulletin of the Chemical Society of Japan 79・6

      Pages: 825-832

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Solid-State ^<29>Si NMR Study of RSiSiR-A Tool for Analyzing the Nature of the Si-Si Bond.2006

    • Author(s)
      V.Kravchenko, R.Kinjo, A.Sekiguchi, M.Ichinohe, R.West, Y S.Balazs, A.Schmidt, M.Karni, Y.Apeloig
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 14472-14473

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A (Tetrasilacyclobutadiene)tricarbonyliron complex [η^4-(^tBu_2MeSi)_4Si_4]Fe(CO)_3 : The Silicon Cousin of Pettit (Cyclobutadiene)tricarbonyliron complex (η^4-H_4C_4)Fe(CO)_3.2006

    • Author(s)
      K.Takanashi, V.Ya.Lee, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Angewandte Chemie, International Edition 45

      Pages: 3269-3272

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The Chemistry of Disilyne with a Genuine Si-Si Triple Bond : Synthesis, Structure, and Reactivity.2006

    • Author(s)
      A.Sekiguchi, M.Ichinohe, R.Kinjo
    • Journal Title

      Bulletin of the Chemical Society of Japan 79

      Pages: 825-832

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Conversion of Disilenide into Silene : Silyl Anion-substituted Silene by a Sila-Peterson-type Reaction from an sp^2-type Silyl Anion.2006

    • Author(s)
      S.Inoue, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Angewandte Chemie, International Edition 46, (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Stable Cyclic Silenes from Reaction of Disinides with Carboxylic Acid Chlorides.2006

    • Author(s)
      I.Bejan, D.Gccl, S.Inoue, M.Ichinohe, A.Sekiguchi, D.Scheschkewitz
    • Journal Title

      Angewandte Chemie, International Edition 46, (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Tetrasilacyclobutadiene (^tBu_2MeSi)_4Si_4 : A New Ligand for Transition Metal Complexes2005

    • Author(s)
      Kazunori Takanashi
    • Journal Title

      Journal of the American Chemical Society 127・16

      Pages: 5768-5769

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Cyclotrisilenylium Ion : The Persilaaromatic Compound2005

    • Author(s)
      Masaaki Ichinohe
    • Journal Title

      Journal of the American Chemical Society 127・28

      Pages: 9978-9979

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The Heavy Analogue of CpLi : Lithium 1,2-Disila-3-germacyclopentadienide, a 6π-Electron Aromatic System2005

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Journal of the American Chemical Society 127・38

      Pages: 13142-13143

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] SiGe_2 and Ge_3 : Cyclic Digermenes that Undergo Unexpected Ring-Expansion reactions2005

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Angewandte Chemie, International Edition 44・36

      Pages: 6378-6381

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Reaction of Dilithiosilane R_2SiLi_2 and -germane R_2GeLi_2(R = SiMe^tBu_2 with MesBCl_2 (Mes = 2,4,6-trimethylphenyl : Evidence for the Formation of Silaborene R_2Si=BMes and Germaborene R_2Ge=BMes2005

    • Author(s)
      Norio Nakata
    • Journal Title

      Chemistry Letters 34・4

      Pages: 582-583

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Disilenyl Anions Derived from Reduction of Tetrakis(di-tert-butylmethylsilyl)disilene with Metal Naphthalenide through Disilene Dianion Intermediate : Synthesis and Characterization2005

    • Author(s)
      Shigeyoshi Inoue
    • Journal Title

      Chemistry Letters 34・11

      Pages: 1564-1565

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Tetrasila-1,3-butadiene and its transformation to disilenyl anions2005

    • Author(s)
      Masaaki Ichinohe
    • Journal Title

      Silicon Chemistry 3

      Pages: 111-116

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Solid-State ^<29>Si NMR Study of RSiSiR - A Tool for Analyzing the Nature of the Si-Si Bond2005

    • Author(s)
      Victoria Kravchenko
    • Journal Title

      Journal of the American Chemical Society 128・45

      Pages: 14472-14473

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Tetrasilacyclobutadiene (^tBu_2MeSi)_4Si_4 : A New Ligand for Transition Metal Complexes.2005

    • Author(s)
      K.Takanashi, V.Ya.Lee, T.Matsuno, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 5768-5769

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Cyclotrisilenylium Ion : The Persilaaromatic Compound.2005

    • Author(s)
      M.Ichinohe, M.Igarashi, K.Sanuki, A.Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 9978-9979

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The Heavy Analogue of CpLi : Lithium 1,2-Disila-3- germacyclopentadienide, a 6-Electron Aromatic System.2005

    • Author(s)
      V.Ya.Lee, R.Kato, M.Ichinohe, Akira Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 13142-13143

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] SiGe_2 and Ge_3 : Cyclic Digermenes that Undergo Unexpected Ring-Expansion reactions.2005

    • Author(s)
      V.Ya.Lee, H.Yasuda, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Angewandte Chemie, International Edition 44

      Pages: 6378-6381

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Reaction of Dilithiosilane R_2SiLi_2 and-germane R_2GeLi_2 (R=SiMe^tBu_2) with MesBCl_2 (Mes=2,4,6-trimethylphenyl) : Evidence for the Formation of Silaborene R_2Si=BMes and Germaborene R_2Ge=BMes.2005

    • Author(s)
      N.Nakata, R.Izumi, V.Ya.Lee, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Chemistry Letters 34

      Pages: 582-583

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Disilenyl Anions Derived from Reduction of Tetrakis(di-tert-butylmethylsilyl)disilene with Metal Naphthalenide through Disilene Dianion Intermediate : Synthesis and Characterization.2005

    • Author(s)
      S.Inoue, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Chemistry Letters 34

      Pages: 1564-1565

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Tetrasila-1,3-butadiene and its transformation to disilenyl anions.2005

    • Author(s)
      M.Ichinohe, K.Sanuki, S.Inoue, A.Sekiguchi
    • Journal Title

      Silicon Chemistry 3

      Pages: 111-116

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A Stable Compound Containing a Silicon-Silicon Triple Bond2004

    • Author(s)
      Akira Sekiguchi
    • Journal Title

      Science 305

      Pages: 1755-1757

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Cyclobutadiene Dianions Consisting of Heavier Group 14 Elements : Synthesis and Characterization2004

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Journal of the American Chemical Society 126・15

      Pages: 4758-4759

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 1,3-Disila-2-gallata- and -indataalleneic Anions [>Si=M=Si<]^- Li^+ (M = Ga, In) : Compounds Featuring Double Bonds Between Elements of Groups 13 and 142004

    • Author(s)
      Norio Nakata
    • Journal Title

      Journal of the American Chemical Society 126・16

      Pages: 5058-5059

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The Isolable Anion Radical of Blue Disilene (^1Bu_2MeSi)_2Si=Si(SiMe^tBu_2)_2 Formed upon One Electron Reduction : Synthesis and Characterization2004

    • Author(s)
      Akira Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 126・31

      Pages: 9626-9627

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The First Bicyclo[1.1.0]butane Dianion of Heavier Group 14 Elements2004

    • Author(s)
      Vladimir Ya. Lee
    • Journal Title

      Angewandte Chemie, International Edition 43・48

      Pages: 6703-6705

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Disilenyllithium from Tetrasila-1,3-butadiene : A Silicon Analogue of a Vinyllithium2004

    • Author(s)
      Masaaki Ichinohe
    • Journal Title

      Organometallics 23・13

      Pages: 3088-3090

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Photochemical Generation of Halo(silyl)silylene : Spectroscopic Observation and Reactivity2004

    • Author(s)
      Takashi Tanaka
    • Journal Title

      Chemistry Letters 33・11

      Pages: 1420-1421

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 三重結合ケイ素化合物ジシリン2004

    • Author(s)
      関口 章
    • Journal Title

      21世紀の有機ケイ素化学-機能性物質科学の宝庫-

      Pages: 16-21

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] ポリシランデンドリマー2004

    • Author(s)
      一戸 雅聡
    • Journal Title

      21世紀の有機ケイ素化学-機能性物質科学の宝庫-

      Pages: 107-112

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Stable Compound Containing a Silicon-Silicon Triple Bond.2004

    • Author(s)
      A.Sekiguchi, R.Kinjo, M.Ichinohe
    • Journal Title

      Science 305

      Pages: 1755-1757

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Cyclobutadiene Dianions Consisting of Heavier Group 14 Elements : Synthesis and Characterization.2004

    • Author(s)
      V.Ya.Lee, K.Takanashi, T.Matsuno, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 126

      Pages: 4758-4759

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 1,3-Disila-2-gallata-and-indataalleneic Anions [>Si=M=Si<]-Li+(M=Ga, In): Compounds Featuring Double Bonds Between Elements of Groups 13 and 14.2004

    • Author(s)
      N.Nakata, R.Izumi, V.Ya.Lee, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Journal of the American Chemical Society 126

      Pages: 5058-5059

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The Isolable Anion Radical of Blue Disilene (^tBu_2MeSi)_2Si=Si(SiMe^tBu_2)_2 Formed upon One Electron Reduction : Synthesis and Characterization.2004

    • Author(s)
      A.Sekiguchi, S.Inoue, M.Ichinohe, Y.Arai
    • Journal Title

      Journal of the American Chemical Society 126

      Pages: 9626-9629

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The First Bicyclo[1.1.0]butane Dianion of Heavier Group 14 Elements.2004

    • Author(s)
      V.Ya.Lee, K.Takanashi, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Angewandte Chemie, International Edition 43

      Pages: 6703-6705

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Disilenyllithium from Tetrasila-1,3-butadiene : A Silicon Analogue of a Vinyllithium.2004

    • Author(s)
      M.Ichinohe, K.Sanuki, S.Inoue, A.Sekiguchi
    • Journal Title

      Organometallics 23

      Pages: 3088-3090

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Photochemical Generation of Halo(silyl)silylene : Spectroscopic Observation and Reactivity.2004

    • Author(s)
      T.Tanaka, M.Ichinohe, A.Sekiguchi
    • Journal Title

      Chemistry Letters 33

      Pages: 1420-1421

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Disilyne having Silicon-Silicon Triple Bond2004

    • Author(s)
      A.Sekiguchi, M.Ichinohe
    • Journal Title

      Organnosilicon Chemistry in 21st Century -The Treasury of Functional Material Science-(ed by K.Tamao)(CMC Publishing, Tokyo) Chapter 1

      Pages: 16-21

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Polysilane-dendorimer2004

    • Author(s)
      M.Ichinohe, A.Sekiguchi
    • Journal Title

      Organnosilicon Chemistry in 21st Century -The Treasury of Functional Material Science-(ed by K.Tamao)(CMC Publishing, Tokyo) Chapter 2

      Pages: 107-112

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

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Published: 2008-05-27  

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