臺灣博碩士論文加值系統

摘 要
Pummerer反應通常是利用sulfoxide和酸或酸酐進行反
應，經由活性的sulfoxide，形成thionium ion與親核性試劑
反應在碳上，產生a-置換sulfide而稱之。
近來，由於高價碘試劑它的毒性低、使用方便、及容易
處理，因此被廣泛地使用在有機合成上，為了繼續探討相關
的高價碘(III)化學及雜環的合成應用，我們計劃利用高價碘
試劑phenyliodine(III) bis(trifluoroacetate) (PIFA)進行sulfides
的Pummerer-type反應，應用於sarmentine與ethyl 1,2,3,4-tetr-
ahydroisoquinoline-1-carboxylates衍生物的製備。

ABSTRACT
The Pummerer reaction of sulfoxides normally proceeds via an activated
sulfoxide and then a thionium ion which reacts with a nucleophile at carbon
to afford an a-substituted sulfide.
Recently, hypervalent iodine reagents have been used extensively in orga-
nic synthesis due to their low toxicity, ready availability and easy handling.As
a continuation of our studies concerning hypervalent iodine(III) chemistry and
its application to the synthesis of heterocycles. We report here that the Pummer-
er-type reaction of sulfides using phenyliodine(III) bis(trifluoroacetate) (PIFA) h-
ave been applied to prepare sarmentine and ethyl 1,2,3,4-tetrahydroisoquinoline-
1-carboxylates derivatives.

目 錄
頁次
一、中文摘要 …………………………………………………… 1
二、英文摘要 …………………………………………………… 2
三、總論 …………………………………………………… 3
四、各論
第一章 利用PIFA進行Pummerer-type反應合成天然物sarmentine
…………………………………………………… 5
第二章 利用PIFA進行Pictet-Spengler縮合反應合成ethyl
1,2,3,4-tetrahydroisoquinoline
…………………………………………………… 16
五、結論 …………………………………………………… 19
六、實驗部分 …………………………………………………… 20
七、參考文獻 …………………………………………………… 37

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