本論文分為兩大主題，利用有機膦試劑對非環狀結構的 α,β-不飽和雙酮衍生物進行 β 位醯化反應及探討由多官能性的磷兩性離子經由分子內選擇性的 Wittig 反應合成多取代苯并呋喃和呋喃[3,2-c]香豆素等。
第一部分：本實驗室開發一系列非環狀結構的 α,β-不飽和雙酮衍生物，其藉由有機膦試劑進行 β 位醯化反應，且結構擺脫過去環張力的限制，並從中探討了過去呋喃產物的生成及副產物對反應的影響，最後藉由時間的控制得到主要產物。
關鍵字；α,β-不飽和雙酮衍生物、有機膦試劑、β 位醯化反應。
第二部分：本實驗室衍生化自行開發的磷兩性離子化合物，並有效的控制此兩性離子行 Wittig 反應的選擇性，且穩定的捕抓其反應過程中所生成的中間體，再利用此中間體性質趨向的不同，合成苯并呋喃或是呋喃[3,2-c]香豆素衍生物，此選擇性的控制在化學領域上相當的新穎，且皆可得到相當良好的結果。
關鍵字；磷兩性離子化合物、化學選擇性、Wittig 反應、苯并呋喃或是呋喃[3,2-c]香豆素。

The thesis is divided into two parts： In the first part, We have developed an organophosphane direct β-acylation of α,β-unsaturated-1,3-diketones derivative under mild conditions. It’s different from our previous studies of β-acylation that caused by ring strain effect. Due to this kind of concept we could afford the single isomers (Z-form) product. Furthermore, β-acylation products or furans products could be controlled by the reaction time .
Key: α,β-unsaturated-1,3-diketones、β-acylation、furans
In the second part, chemoselective synthesis of substituted benzofurans and furo[3,2-c]coumarins from functional phosphorus zwitterions via intramolecular Wittig reactions is described. Based on our previous studies, a phosphine-triggered intramolecular Wittig reaction with high efficiency via phosphorus zwitterions as key intermediates has been developed. The studies included chemoselectivities of acylations and intramolecular Wittig reactions. Besides, the mechanism study and expanding substrate was been clarified in our research. Following different addition sequence of the acyl chloride and phosphine reagent, the corresponding fused-heteroaryl derivatives can be synthesized chemoselectively, which will be published in due course.
Key: phosphorus zwitterions、chemoselectively、benzofurans、furo[3,2-c]coumarins.

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