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    National Tsing Hua University Institutional Repository > 理學院 > 化學系 > 期刊論文 >  [2 + 2] Dimerization of norbornadiene and its derivatives in the presence of nickel complexes and zinc metal

    Please use this identifier to cite or link to this item: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/57581

    Title: [2 + 2] Dimerization of norbornadiene and its derivatives in the presence of nickel complexes and zinc metal
    Authors: HUANG, DJ;CHENG, CH
    教師: 鄭建鴻
    Date: 1995
    Publisher: Elsevier
    Relation: Journal of Organometallic Chemistry, Elsevier, Volume 490, Issues 1-2, 22 March 1995, Pages C1-C7
    Keywords: Nickel
    Abstract: Norbornadiene undergoes [2 + 2] reaction in THF in the presence of NIX, and zinc metal powder to give an exo-trans-exo dimer and an exo-trans-exo-trans-exo trimer. In these products, the norbornadiene molecules are linked to each other by forming cyclobutane rings with all cyclobutane carbons occupying exo positions relative to the bridging carbons on the two norbornadiene fragments. Polymerization of norbornadiene occurs if the catalyst NiX(2) is replaced by Ni(PPh(3))(2)Cl-2. 1,4-Dihydro-1,4-epoxynaphthalene, 5,8-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene, 5-methoxy-1,4-dihydro-1,4-epoxynaphthalene and methyl 1,4-dihydro-1,4-iminonaphthalene-9-carboxylate also dimerize to give exo-trans-exo products in excellent yields in toluene in the presence of Ni(PPh(3))(2)Cl-2 and Zn powder. For the dimerization products of 5-methoxy-1,4-dihydro-1,4-epoxynaphthalene cis and trans isomers with respect to the orientation of methoxy groups in about 1:1 ratio were observed. Under similar reaction conditions for the dimerization of norbornadiene, norbornene undergoes reductive dimerization to afford a product which consists of two norbornyl groups. The structure of this product is also exo-rrans-exo.
    URI: http://www.elsevier.com/
    Appears in Collections:[化學系] 期刊論文

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