本篇研究將探討具有醯胺(Amide group)或是羥基(Hydroxyl group)的重氮化合物之合成，以及分別對其進行分子內N-H或O-H插入反應(Intramolecular N-H / O-H insertion)之結果。
我們使用實驗室開發的新型氮轉移試劑，能夠合成出不同胺基酸側鏈並且具有醯胺或是羥基的重氮化合物，在具有醯胺官能基的例子中得知必須藉由羰基(Carbonyl group)等較強的拉電子基來降低二級胺的親核性，才能避免二級胺與氮轉移試劑進行副反應；而具有羥基之重氮化合物則是在氮轉移反應中觀察到形成大量染料，推測為影響產率的主要因素。
第一個目標產物為常見於藥物結構中的2-嗎啉酮衍生物(Morpholin-2-one)，可透過重氮化合物進行分子內插入反應獲得，在本篇研究中成功合成具有不同胺基酸側鏈之重氮化合物，解決了過去文獻中取代基被限制的問題，並且可以在溫和的條件下進行分子內N-H插入反應，可惜的是在1, 2-氫轉移反應的競爭下，由於立體障礙、醯胺親核性較弱，以及距離金屬卡賓碳較遠等空間上的不利因素，造成大部分具有CH2側鏈的例子形成共振穩定性高的烯烴副產物。
第二個目標產物則是在生醫材料的領域中做為聚合物之單體的對二氧環己酮衍生物(p-Dioxanone)，已有研究顯示若在3號碳的位置接上甲基，可以透過比例來調整其相對應的共聚合物之材料特性，但是目前進行3號碳位置取代之研究非常少，其中3-甲基-對二氧環己酮的合成產率僅有20-50%。因此在本篇研究中合成具有羥基的重氮化合物來進行分子內O-H插入反應，成功獲得具有苄基保護之麩胺酸側鏈的對二氧環己酮衍生物，其餘的例子中則是產生烯烴產物。
除此之外我們嘗試降溫以及變換金屬催化劑，皆無法改善分子內插入反應失敗的例子，但是若同時將親核性以及空間上的不利因素排除，就能夠將主要反應由1, 2-氫轉移改變為分子間插入反應(Intermolecular insertion)。因此總和以上所述，我們認為此類具有CH2側鏈之重氮化合物比起分子內插入反應，更適合進行分子間插入反應。

By using the N-transfer reagent developed in our laboratory, we have successfully synthesized diazo compounds with amino acid side chains and amide or hydroxyl functional group. In the case of amide functional group, it revealed that the nucleophilicity of secondary amine must be reduced by strong electron-withdrawing groups such as carbonyl group, so as to avoid the unexpected side product in N-transfer reaction; The diazo compounds with hydroxyl group were found to generate a large amount of dyes during N-transfer reaction, which might be the main factor causing the yield decreased.
Morpholin-2-ones are among the commonly encountered scaffolds in drugs relevant. In this study, diazo compounds with different amino acid side chains and amide functional group were synthesized for intramolecular N-H insertion. It solved the problem of limited substituents in the previous literature, and could carry out intramolecular N-H insertion reaction under mild conditions.
Previous studies have shown that the properties of poly-p-dioxanone can be adjusted through the substituents on carbon atom at position 3. Therefore, in this study, diazo compounds with hydroxyl group were synthesized for intramolecular O-H insertion reaction, and p-dioxanone derivatives with benzyl group protected glutamic acid side chain were successfully obtained.
Moreover, we tried to reduce the temperature and change the metal catalyst, but neither improved the intramolecular insertion reaction. However, if the nucleophilicity and spatial disadvantages are excluded at the same time, the major reaction could be changed from 1, 2-hydride shift to intermolecular insertion reaction. In summary, compared with intramolecular insertion reaction, we think that the diazo compounds with CH2 side chain are more suitable for intermolecular insertion reaction.

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