我們發展出了一套能將1,6-烯炔化合物及重氮化合物，在溫和條件金金屬催化下，可以合成出E/Z form乙烯基二環[3.1.0]己烷衍生物。接下來藉由銠金屬催化E/Z form乙烯基二環[3.1.0]己烷衍生物，依據基質特性的不同，會生成兩種不同形式的產物，銠金屬會先插入三元環的碳碳鍵中，若此時中間體發生1,3–位移反應，則會生成四氫-1H-環戊烯併呋喃衍生物；若中間體發生β-氫消除反應則會生成含有共軛雙烯結構的產物，且兩者都有不錯的產率。

The reaction of a variety of unsaturated bond-containing 1,6-enynes with diazo compounds in the presence of [(IPr)AuBF4] as catalyst precursor at room temperature leads to the general formation of alkenylbicyclo[3.1.0]hexane derivatives with good yields, which were, afterwards, when heated in o-xylene solvent in the presence of [Rh(CO)2Cl]2 as catalyst at 150 0C affords two types of product, depending on the type of tether in alkenylbicyclo[3.1.0]hexane derivatives. In the first case, rhodium insertion into three member ring followed by 1,3-shift gives tetrahydro-1H-cyclopenta[c]furan. Whereas, in the second case, rhodium insertion and beta-hydride elimination affords conjugate diene compound. Both cases give good yields.

目錄
謝誌 ..........................................I
中文摘要 .......................................II
英文摘要 ......................................III
目錄 ..........................................IV
圖目錄 .......................................VII
表目錄 ........................................IX
附錄目錄 ........................................X
英文縮寫對照表 ................................XVI

目錄
第一節 緒論 ...................................1
1.1 環化加成反應 ...............................1
1.2 過渡金屬催化應用於環化加成反應 ..............1
1.4 葆森–侃德反應 (Pauson–Khand reaction) ........2
1.5 以異腈代替一氧化碳的葆森–侃德反應 ...........4
1.6 以重氮化合物作為環化加成反應單碳單元 .........5
1.7 乙烯基環丙烷重排形成環戊稀之反應 ............7
第二節 實驗動機及概述 ..........................8
第三節 結果與討論 .............................10
3.1 反應條件最佳化 ...........................10
3.2 1,6–烯炔醚類衍生物與單邊取代重氮化合物反應之官能基容忍度探討 ...........................................11
3.3 1,6–烯炔胺類衍生物與雙邊取代重氮化合物反應之官能基容忍度探討 ...........................................13
3.4 1,6–烯炔胺類衍生物與單邊取代重氮化合物反應之官能基容忍度探討 ...........................................14
3.5 一鍋化反應之探討 ..........................15
3.6 金催化反應的官能基限制 ....................16
3.7 反應機構 .................................17
第四節 結論 ..................................19
第五節 實驗部分 ...............................20
5.1 實驗藥品之中英文對照表 .....................20
5.2 實驗之一般操作 ............................22
5.3 實驗基質之合成 ............................24
5.4 催化反應之操作 ............................31
5.5 一鍋化反應之操作 ..........................33
5.6 光譜資料 .................................34
5.7 X-ray 結構鑑定 ...........................63
第六節 參考文獻 ...............................72

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