National Tsing Hua University Institutional Repository:Stereoselective [2 + 2 + 2] cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes catalyzed by nickel complexes: First transition metal-mediated synthesis of isobenzofuran and isoindole precursors
English  |  正體中文  |  简体中文  |  全文笔数/总笔数 : 54367/62174 (87%)
造访人次 : 14544527      在线人数 : 99
RC Version 6.0 © Powered By DSPACE, MIT. Enhanced by NTHU Library IR team.
搜寻范围 查询小技巧:
  • 您可在西文检索词汇前后加上"双引号",以获取较精准的检索结果
  • 若欲以作者姓名搜寻,建议至进阶搜寻限定作者字段,可获得较完整数据
  • 进阶搜寻
    National Tsing Hua University Institutional Repository > 理學院 > 化學系 > 期刊論文 >  Stereoselective [2 + 2 + 2] cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes catalyzed by nickel complexes: First transition metal-mediated synthesis of isobenzofuran and isoindole precursors


    jsp.display-item.identifier=請使用永久網址來引用或連結此文件: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57528


    题名: Stereoselective [2 + 2 + 2] cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes catalyzed by nickel complexes: First transition metal-mediated synthesis of isobenzofuran and isoindole precursors
    作者: Sambaiah,Thota;Huang,Daw-Jen;Cheng,Chien-Hong
    教師: 鄭建鴻
    日期: 2000
    出版者: Royal Society of Chemistry
    關聯: Journal- Chemical Society Perkin Transactions 11, Royal Society of Chemistry, Issue 2, 2000, Pages 195-203
    关键词: Thermal effects
    Catalysis
    Toluene
    Stereochemistry
    Polymerization
    Synthesis
    Olefins
    摘要: Oxabenzonorbornadiene (1a) reacted with various alkynes in the presence of Ni(PPh3)2Cl2, PPh3 and zinc powder in toluene to give two common products 2a and 2b regardless of the alkyne used. The formation of 2a and 2b are proposed to be from the Diels-Alder reaction of la and isobenzofuran. The latter is generated from the retro Diels-Alder reaction of [2 + 2 + 2] cycloadducts of la and alkynes catalyzed by the nickel system. A series of nickel-catalyzed [2 + 2 + 2] cycloadducts (4a-j and 5a-d) of oxa- and azabenzonorbornadienes (1a-d) with terminal alkynes were isolated at temperatures -5-18 °C. Similarly, hepta-1,6-diyne and octa-1,7-diyne reacted with 1a and 1d to give novel pentacyclic [2 + 2 + 2] cycloadducts 6a-d in 62-75% yields. These products are convenient isobenzofuran and isoindole precursors that react with various dienophiles to afford the corresponding Diels-Alder adducts. In addition, the [2 + 2 + 2] cycloadducts may be used as precursors for the synthesis of aromatic compounds. For example, the reaction of la with methyl but-2-ynoate catalyzed by the nickel system provided aromatic compound 3 in 94% yield. In this reaction, la is a 'masked acetylene' providing an acetylene moiety to 3.
    URI: http://www.rsc.org/
    http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57528
    显示于类别:[化學系] 期刊論文

    文件中的档案:

    档案 描述 大小格式浏览次数
    2010326010004.pdf204KbAdobe PDF802检视/开启


    在NTHUR中所有的資料項目都受到原著作權保護,僅提供學術研究及教育使用,敬請尊重著作權人之權益。若須利用於商業或營利,請先取得著作權人授權。
    若發現本網站收錄之內容有侵害著作權人權益之情事,請權利人通知本網站管理者(smluo@lib.nthu.edu.tw),管理者將立即採取移除該內容等補救措施。

    SFX Query

    與系統管理員聯絡

    DSpace Software Copyright © 2002-2004  MIT &  Hewlett-Packard  /   Enhanced by   NTU Library IR team Copyright ©   - 回馈