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    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


    Please use this identifier to cite or link to this item: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57528


    Title: 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
    Authors: Sambaiah,Thota;Huang,Daw-Jen;Cheng,Chien-Hong
    教師: 鄭建鴻
    Date: 2000
    Publisher: Royal Society of Chemistry
    Relation: Journal- Chemical Society Perkin Transactions 11, Royal Society of Chemistry, Issue 2, 2000, Pages 195-203
    Keywords: Thermal effects
    Catalysis
    Toluene
    Stereochemistry
    Polymerization
    Synthesis
    Olefins
    Abstract: 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
    Appears in Collections:[化學系] 期刊論文

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