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    National Tsing Hua University Institutional Repository > 理學院 > 化學系 > 期刊論文 >  Regioselective haloaromatization of 1,2-bis(ethynyl)benzene via halogen acids and PtCl2. Platinum-catalyzed 6 pi electrocyclization of 1,2-bis(1 '-haloethenyl)benzene intermediates


    Please use this identifier to cite or link to this item: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57893


    Title: Regioselective haloaromatization of 1,2-bis(ethynyl)benzene via halogen acids and PtCl2. Platinum-catalyzed 6 pi electrocyclization of 1,2-bis(1 '-haloethenyl)benzene intermediates
    Authors: Lo CY;Kumar MP;Chang HK;Lush SF;Liu RS
    教師: 劉瑞雄
    Date: 2005
    Publisher: American Chemical Society
    Relation: Journal of Organic Chemistry,American Chemical Society,Volume: 70,Issue: 25,Pages: 10482-10487,Published: DEC 9 2005
    Keywords: ENYNE-ALLENES
    ANIONIC CYCLOAROMATIZATION
    BERGMAN CYCLIZATION
    NEOCARZINOSTATIN CHROMOPHORE
    Abstract: Treatment of 1,2-bis(ethynyl)benzene (1) with aqueous HX (X = Br, I) in hot 3-pentanone (100105 degrees C, 2 h) afforded 1,2-bis(1'-baloethenyl)benzene species 2-Br and 2-I in 98% and 95% yields, respectively. The hydrochlorination of endiyne 1 failed to proceed at elevated temperature but was implemented efficiently by PtCl2 (5 mol %) in hot 3-pentanone (100 degrees C, 2 h) to give 1,2-bis(1'-chloroethenyl)benzene 2-Cl in 80% yield. In the presence of PtCl2 (5 mol %), these halides 2-Cl, 2-Br, and 2-I were subsequently converted to 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in the mother solution via sequential 6-pi electrocyclization and dehalogenation reactions. PtCl2 (5 mol %) also effected direct haloaromatization of endiyne 1 with HX (X = Cl, Br, 1) and gave 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in 64-71% yields. This investigation reports the scope and the regioselectivity of haloaromatization of various enediynes catalyzed by PtCl2.
    URI: http://pubs.acs.org/
    http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57893
    Appears in Collections:[化學系] 期刊論文

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