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研究生: 高國席
論文名稱: β-硝基苯乙烯系列和有機鋰或有機銅鋰試劑反應之探討
指導教授: 姚清發
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
畢業學年度: 85
語文別: 中文
論文頁數: 94
中文關鍵詞: β-硝基苯乙烯有機鋰
論文種類: 學術論文
相關次數: 點閱:153下載:0
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  • β-Nitrostyrene及其衍生物與有機鋁試劑反應後經稀酸水溶液水解後可得到1,4-加成的產物,如硝基烷類。然而如果將反應所形成之中間體nitronates加入冰冷的濃氫鹵酸水溶液中,預期會進行Nef或Meyer反應而得到羰基或酸的化合物。但實驗分析結果卻意外地發現鹵素陰離子可以抓住中間體 nitronates而形成hydroximoyl haIides。hydroximoyI halides 在鹼性條件下可脫去HX而形成nitrile oxides。nitrile oxides會與烯或炔類進行1,3-dipolar cycloaddition 反應而生成具有立體專一性或高立體選擇性的產物2-isoxazolines或isoxazoles。
    β-Nitrostyrene 及其衍生物與有機銅鋰試劑反應後經稀酸水溶液水解則得到1,4-加成的產物,如硝基烷類。但如果將反應所形成之中間體nitronates加入冰冷的濃氫鹵酸水溶液中則得到 hydroximoyl halides和硝基烷的混合物。

    β-Nitrostyrenes can react with Organolithium reagents to form 1,4-addition products such as primary nitroalkanes after workup with diluie aqueous acid solution. It is expected to under go Nef or Meyer reaction to generate the carbonyl compounds or carboxylic acids if the intermediate-nitronates are slowly added to the ice cold concentrated HX(aq) solution Surprisingly, the hydroximoyl halides are formed when the halide ions trap the reactive intermediates. Hydroximoyl halides can be converted into nitrile oxides with base. It is known that nitrile oxides undergo 1,3-dipolar cycloaddition with alkenes or alkynes to generate stereospecific or stereoselective of 2-isoxazolines or isoxazoles.
    Reactions of β-nitrostyrenes with Lithium Organocuprates will generate nitroalkanes after workup with dilute aqueous acid solution. If the intermediates are slowly added to the ice cold concentrated HX(aq) solution, the products are hydroximoyl halides and nitroalkanes.

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