本論文主要分為兩大部分，第一部分為利用苯炔與亞胺經由 π 鍵的嵌入反應合成苯并噁嗪化合物，第二部分為經由化學選擇性氧-醯化反應或氮-醯化反應與分子內 Wittig 反應合成三取代噁唑化合物或高官能基苯并呋喃化合物。
第一部分 : 苯炔為高活性的反應中間體，因其多樣化的反應形式總是吸引許多化學家的注意，我們嘗試利用它與同樣高活性且缺電子的氮-醯基亞胺反應，出乎我們意料之外的，得到的產物為經由 π 鍵的嵌入反應形成的苯并噁嗪化合物，我們也可以使用具取代基的芳香炔化合物與氮-醯基亞胺進行反應，來探討其化學選擇性。
第二部分 : 噁唑化合物與苯并呋喃化合物的合成，在有機合成領域之中為重要的研究重點之一，我們可以藉由添加不同的醯氯試劑，像是立體阻礙較大的三甲基乙醯氯 (t-BuCOCl) 或高活性的三氟乙酸酐 (TFAA) 與同時具有兩個反應官能基的亞胺起始物來進行反應，控制其化學選擇性分別經由化學選擇性氮-醯化反應得到苯并呋喃化合物 (t-BuCOCl) 或經由化學選擇性氧-醯化反應得到噁唑化合物 (TFAA)。

The thesis is devided into two parts:
Part 1
Synthesis of 1,3-Benzoxazines via π-insertion reactions of Arynes and N-Acyl imines.

Because arynes are highly reactive species and can undergo a variety of transformations, their chemistry attract chemist a lot of attention. We have successfully utilized the eletron-deficient N-acyl imines to trap the in situ generated intermediates, benzyne, to obtain the corresponding benzoxazine derivatives in moderate yields. These unprecedented reactions are assumed to be via an unexpected [2+2] cycloaddtion of N-acyl imine and benzyne as the key step.

Part 2
Chemoselective Intramolecular Wittig Reactions for the Synthesis of Oxazoles and Benzofurans.

A chemoselective approach was developed for the synthesis of highly functionalized oxazoles and benzofurans using an intramolecular Wittig reaction as the key step. By choosing proper trapping reagent or method of addition of reagents, chemoselectivity can be controlled toward either oxazole or benzofuran derivatives.

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