本論文主要分為兩個部分，第一部分是研究本實驗室所發展之碘化反應，對步驟中所加入之碘化鈉與間-氯過苯甲酸做更深入之探討。為了證明碘化鈉與間-氯過苯甲酸為有效碘正離子來源，我們選用分子內同時具有親核性的氧原子與不飽和鍵結構的化合物 38及71 來進行碘正離子引導氧原子環化反應，使不飽和鍵結構能與碘化鈉與間-氯過苯甲酸形成碘正架橋中間體結構，誘使氧原子攻擊而產生碘化環化產物。
第二部分則研究以各種非掌性或掌性二級胺先與起始物14 或 23進行反應得烯胺後，再與碘化鈉及間-氯過苯甲酸作用而得到α-碘基酮。
本實驗室碘化鈉與間-氯過苯甲酸確實為有效的碘正離子來源，且反應條件溫和，期望未來可以更廣泛的應用在有機合成反應中。

The thesis consists of two chapters. The first chapter describes the iodination with NaI and m-CPBA developed from our lab. In order to prove that NaI and m-CPBA are effective in forming iodonium ion, we used compound 38 or 71 as starting material which underwent iodination with NaI and m-CPBA to give iodonium intermediate. And then iodonium intermediate underwent anti cyclization by suitably placed alcoholic or carboxylic group lead to lactone 39 or cyclic ether 73 .
The second chapter describes the α-iodination of enamines. Treatment of cyclohexanone 14 or cyclopentanone 23 with various secondary amines underwent dehydration to generate enamine. We used these enamines as starting material, which underwent α-iodination with NaI and m-CPBA to give α-iodo ketone.
Surely NaI and m-CPBA are effective in forming iodonium ion, we hope that this mild iodination method can be used extensively in organic synthesis.

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