臺灣博碩士論文加值系統

本論文成功的以化合物8及化合物23為起始物經Wittig
反應，合成出骨架上含有的兩個氧的籠狀化合物15及24。
利用籠狀化合物8進行親電子性及親核性反應，探討反應之立體面向選擇性，發現其以syn-attack為主產物。
將diols 30,35,39,42,47,51 溶於甲醇中，在-78℃下進行臭氧裂解反應可得化合物31,36,40,43, 48,52.
在Amberlyst-15的作用下可成功使化合物31, 36, 40, 43, 48, 52及2,5-Dimethoxy-2,5-dihydrofuran （mixture of cis and trans isomers）進行重排反應，進而得到其重排產物。
Amberlyst-15與TiCl4相較下為一溫和、不具危險性且方便、便宜之試劑，其為固體顆粒，欲終止反應時，僅需經由過濾即可移除之。

π-Facial Selectivity of Dioxa-cages and
Chemical Transformation of Dimethoxy Dioxa-cages
Student：Hui-Hsueh Chung Advisor：Dr. Hsien-Jen Wu
Institute of applied Chemistry
Nationl Chiao Tung University
Abstract
The diacetal dioxa-cage compounds15 and 24 from Wittig reaction of compounds 8 and 23 was synthesized successfully.
The reaction of the diacetal dioxa-cage compounds 8 with electrontrophiles gave the corresponding syn-sttack products.
Ozonlysis of diols 30,35,39,42,47,51 in MeOH at -78℃follow by treatment with Me2S and Amberlyst-15gave compounds31,36,40,43, 48
,52.
The reaction of the compounds 31, 36, 40, 43, 48, 52and 2,5-Dimethoxy-2,5-dihydrofuran （mixture of cis and trans isomers）with Amberlyst-15 in dichloromethane gave the hydride rearrangement products.
Amberlyst-15 compare with TiCl4 is a mild、saft、low-priced and convenience catalyst and work-up is exceedingly simply, it only involves filtration of the resin and removel of solvent to obtain product.

目錄
中文摘要……………………………………………………….i
英文摘要………………………………………………………ii
謝誌……………………………………………………………iii
目錄……………………………………………………………iv
圖目錄………………………………………………………….v
第一部份
第一章緒論………………………………………………….2
第二章研究構想………………………………………..….20
第三章結果與討論………………………………………...22
第四章結論………………………………………………...49
第二部份
第一章 緒論…………………………………………………51
第二章 研究構想……………………………………………58
第三章 結果與討論…………………………………………60
第四章 結論…………………………………………………72
第五章 實驗………………………………………………....73
5.1 一般敘述……………………………………………73
5.2 合成步驟及光譜數據………………………………75
第六章 參考文獻…………………………………………...98
附錄一………………………………………………….……105
簡歷………………………………………….………………150

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