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  • 學位論文

New Pathway Towards the Synthesis of Dibenzo[g,p]chrysenes bearing various Functionalities and Studies of their Photophysical and Electronic Properties & Transition Metal Catalyzed Organic Transformations for the Synthesis of Functionalized Carbocyclic Frameworks

指導教授 : 劉瑞雄

摘要


The synthesis of Dibenzo[g,p]chrysenes bearing various functionalities and studies of their photophysical and electronic properties are mentioned in this dissertation. Transition metal-catalyzed organic transformations cycloaddition and cycloisomerization of appropriately functionalized organic molecules are also described in this dissertation. For sake of convenience and better understanding, the thesis is divided into four chapters. In the first chapter a new synthetic pathway to functionalized dibenzo[g,p]chrysenes from bis(biaryl)acetylenes has been described. We also presented variations of the photophysical and electronic properties of dibenzo[g,p]chrysenes by their electron-rich and –defficient substituents, in particular their HOMO-LUMO energy levels, UV absorptions, and fluorescent emissions. The second chapter deals with a novel gold-catalyzed intramolecular [3+2]-cycloadditions of 1-aryl-1-allen-6-enes in CH2Cl2 at 25 oC, which gave cis-fused [4.3.0] carbocyclic compounds selectively. The third chapter describes, a platinum-catalyzed skeletal rearrangement of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes involving new aromatization/1,3-carbonyl shift cascade. This reaction sequence is mechanistically interesting because it involves a 1,3-carbonyl shift. The fourth chapter presents a novel Pt-catalyzed protocol for the synthesis of carbocycles and heterocycles. We presented the oxy effect on chemoselectivity of the carbocyclization of Epoxy-Alkynes.

並列摘要


本論文共分為兩大部分四個章節,第一部分合成一系列具有不同官能基修飾的Dibenzo[g,p]chrysenes,並探討其光學以及電化學性質。第二部分利用過渡金屬錯合物催化環化加成以及環化異構化反應,且可作用在多種不同官能基的有機分子上。 第一章節我們發展出利用雙(聯芳香環)炔類化合物合成出一系列具不同官能基修飾的dibenzo[g,p]chrysenes。並測量了其氧化還原電位,紫外光吸收以及放射光譜進而針對其官能基推拉電子的性質分別在光學,電化學做探討。 第二章節探討了將1-芳香環-1-丙二烯-6-烯類化合物於室溫下利用金金屬催化分子內[3+2]-環化加成反應,可得到具選擇性的順式-駢雙環[4.3.0]環碳化合物。 第三章節我們利用了鉑金屬錯合物催化分子骨架得重排反應將2-環氧基-1-(甲氧烷基-2-炔基)苯化合物經由一連串的芳香環化反應以及1,3羰基轉移反應。此類反應機構非常的特別,其中間包含了1,3羰基轉移反應。 第四章節我們發表了利用鉑金屬錯合物催化有機分子合成出一系列的環碳以及雜環類化合物。此類反應由於oxy effect使得環氧基-炔類化合物在進行環化反應時具有化學選擇性。

參考文獻


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被引用紀錄


林璟平(2008)。協同教學發展國小數學教師PCK之行動研究〔碩士論文,中原大學〕。華藝線上圖書館。https://doi.org/10.6840%2fcycu200800282

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