單硫雙氧籠狀化合物之合成及其羰基之親核加成面向選擇性之研究

Abstract

本論文以骨架上具有三個氧之籠狀化合物18、19分別進行化學轉換，各自得到新型骨架上具有單硫雙氧之籠狀化合物20、21。 利用apex碳上具有羰基之單硫雙氧籠狀化合物20、21之羰基進行親核基加成反應，探討反應之立體面向選擇性，其結果皆得到親核基試劑由硫原子之反面來對羰基進行攻擊而得到之單一產物。我們認為扭張力效應可能是這種面向選擇性的主要因素。

The synthesis of the monothia-dioxa-cage compounds 20 and 21 have been accomplished by chemical transformation from the trioxa-cage compounds 18 and 19. Reactions of the monothia-dioxa-cage compounds 20 and 21 with various nucleophiles exclusively gave the corresponding products which were obtained by nucleophilic addition on the carbonyl group from the face anti to the sulfur atom. The major effect of these results may be attributed to the torsional effect.