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Synthesis and Property of Pi-conjugated Compounds Using Reactive Molecules

Research Project

Project/Area Number 22750045
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKwansei Gakuin University

Principal Investigator

HAMURA Toshiyuki  関西学院大学, 理工学部, 准教授 (20323785)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2011: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords合成有機化学 / π共役系分子 / 物性・機能 / 高反応性分子 / ポリアライン / 官能基選択性 / 時間的反応集積化 / ワンポット合成 / シクロブタアレン / π共役系有機化合物 / ベンザイン / アルキニルリチウム / 多重環状付加 / ポリシクロブタベンゼン / ポリメチレンシクロブタベンゼン
Research Abstract

We developed an efficient and chemoselective generation protocol for a benzyne species and its regioselective functionalization by nucleophilic addition. Importantly, alkynyllithium plays the key roles for this novel benzyne reaction as an efficient initiator for the benzyne generation and a good nucleophile to benzyne. Moreover, we found that thermal isomerization of tricyclobutabenzene offered a highly stereoselective access to stereodefined hexaradialenes, which was trapped with three identical or different dienophiles, allowing a rapid construction of polycyclic aromatic compounds.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (18 results)

All 2012 2011 2010 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (7 results) Remarks (1 results)

  • [Journal Article] Catalytic Generation of Arynes and Trapping by Nucleophilic Addition and Iodination2012

    • Author(s)
      羽村季之、忠田悠、中辻裕也、鈴木啓介
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: vol.51 Pages: 3368-3372

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Generation of Arynes and Trapping by Nucleophilic Addition and Iodination2012

    • Author(s)
      羽村季之
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 51 Issue: 14 Pages: 3368-3372

    • DOI

      10.1002/anie.201108415

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring Expansion of Cyclopropylbenzocyclobutenes En Route to Benzocycloheptenes2011

    • Author(s)
      福井伸明、羽村季之、大森建、鈴木啓介
    • Journal Title

      Chem. Lett

      Volume: vol.40 Pages: 1198-1200

    • NAID

      10029684039

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A domino pericyclic route to polysubstituted salicilic acid derivatives : four sequential processes from enynones and ketene silyl acetals2011

    • Author(s)
      羽村季之、岩田伸、鈴木啓介
    • Journal Title

      Chem. Commun

      Volume: vol.47 Pages: 6891-6893

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Domino Pericyclic Route to Polysubstituted Salicylic Acid Derivatives : Four Sequential Processes from Enynones and Ketene Silyl Acetals2011

    • Author(s)
      羽村季之
    • Journal Title

      Chem.Commun

      Volume: 47 Issue: 24 Pages: 6891-6893

    • DOI

      10.1039/c1cc11758k

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring Expansion of Cyclopropylbenzocyclobutenes En Route to Benzocycloheptenes2011

    • Author(s)
      羽村季之, 福井伸明
    • Journal Title

      Chem.Lett.

      Volume: 40 Issue: 10 Pages: 1198-1200

    • DOI

      10.1246/cl.2011.1198

    • NAID

      10029684039

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Siloxy(trialkoxy) ethane undergoes regioselecitive[2+2] cycloaddition to ynones and ynoates en route to functionalized cyclobutenediones2010

    • Author(s)
      岩田伸、羽村季之、鈴木啓介
    • Journal Title

      Chem. Commun

      Volume: vol.46 Pages: 5316-5318

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Hexaradialenes by Successive Ring Openings of Tris(alkoxy-tricyclobutabenzenes): Synthesis and Characterization2010

    • Author(s)
      篠崎真也、羽村季之、指宿洋介、藤井孝太郎、植草秀裕、鈴木啓介
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: vol.49 Pages: 3026-329

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Siloxy(trialkoxy)ethene Undergoes Regioselecitive [2+2] Cycloaddition to Ynones and Ynoates en route to Functionalized Cyclobutenediones2010

    • Author(s)
      岩田伸
    • Journal Title

      Chem.Commun

      Volume: 46 Pages: 5316-5318

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hexaradialenes via Successive Ring Openings of Trisalkoxy tricyclobutabenzenes : Synthesis and Characterization2010

    • Author(s)
      篠崎真也
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 49 Pages: 2248-2250

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Catalytic Generation of Benzyne Species and Trapping by Nucleophilic Addition and Iodination2011

    • Author(s)
      羽村季之
    • Organizer
      WOCJC-Senior Workshop
    • Place of Presentation
      東京工業大学(招待講演)
    • Year and Date
      2011-11-21
    • Related Report
      2011 Annual Research Report
  • [Presentation] 高反応性分子を駆使した新規π共役系分子の創製2011

    • Author(s)
      羽村季之
    • Organizer
      「有機合成化学を起点とするものづくり戦略」ミニシンポジウム
    • Place of Presentation
      東京大学小柴ホール、日本
    • Year and Date
      2011-11-14
    • Related Report
      2011 Final Research Report
  • [Presentation] 高反応性分子を駆使した新規π共役系分子の創製2011

    • Author(s)
      羽村季之
    • Organizer
      「有機合成化学を起点とするものづくり戦略」ミニシンポジウム
    • Place of Presentation
      東京大学小柴ホール(招待講演)
    • Year and Date
      2011-11-14
    • Related Report
      2011 Annual Research Report
  • [Presentation] Catalytic Generation of Benzyne Species and Trapping by Nucleophilic Addition and Iodination2011

    • Author(s)
      羽村季之
    • Organizer
      WOCJC-Senior Workshop
    • Place of Presentation
      東京工業大学、日本
    • Year and Date
      2011-11-02
    • Related Report
      2011 Final Research Report
  • [Presentation] Hexaradialenes via Successive Ring Openings of Trisalkoxytricyclobutabenzenes : Synthesis, Reactivity, and Characterization2010

    • Author(s)
      羽村季之
    • Organizer
      WOCJC-7
    • Place of Presentation
      Taiwan
    • Year and Date
      2010-09-04
    • Related Report
      2011 Final Research Report
  • [Presentation] 高反応性分子を駆使した新規π共役系分子の創製2010

    • Author(s)
      羽村季之
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学、日本
    • Year and Date
      2010-08-02
    • Related Report
      2011 Final Research Report
  • [Presentation] 高反応性分子を駆使した新規π共役系分子の創製2010

    • Author(s)
      羽村季之
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • Related Report
      2011 Final Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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