臺灣博碩士論文加值系統

本論文對 bis-endo-diol 取代基之 [2.2.1]庚烯衍生物，經由臭氧裂解反應，可合成出骨架上含有三個氧之籠狀化合物。
對 bis-endo-diol 取代基之 [2.2.2]辛烯衍生物及單環己烯衍生物，經由臭氧裂解反應，可合成出單環環化產物。 將 1,4- 對苯菎衍生物與 1,3- 環戊二烯及 1,4- 環己二烯進行 Diels-Alder 反應，將其所產生的 endo 加成產物，使用 NaBH4-CeCl3 試劑進行立體選擇性還原反應，再將此產物經由臭氧裂解反應，可合成出骨架上含有三個氧與雙鍵之籠狀化合物。
本論文利用臭氧裂解反應可合成出籠狀化合物 57。 本論文利用碘誘導環化反應，再經由臭氧裂解反應可合成出籠狀化合物 67、76。
本論文對籠狀化合物 57、67、76 進行面向選擇性研究。

Several novel diacetal teioxa-cages compounds 4, 9a-9c, 14 and 17 are synthesized in a short sequence. Diacetal trioxa-cage where synthesized from norbornene derivative of bis-endo-diol by utilizing a novel ozonolysis reaction as the key step. Ozonolysis of bicyclo[2.2.1]heptenes 3, 8a-8c, 13 and 16in dichloromethane at -78℃ followed by reduction with dimethyl sulfide gave diacetal oxa-cages 4, 9a-9c, 14 and 17 in moderate yields, respectively.
Ozonolysis of bicyclo[2.2.2]octene 19 under the same reaction conditions gave mono-cyclization product 20. Ozonolysis of cyclohexene 29 under the same reaction conditions gave mono-cyclization product 32.
Ozonolysis of p-benzoquinones derivatives 34 ,37 and 40 under the same reaction conditions gave diacetal oxa-cages 35 ,38 and 41 in moderate yields, respectively.
Synthesis of carbonyl oxa-cage 57 is by using ozonolysis reaction. Synthesis of carbonyl oxa-cages 67 and 76 is by using iodocyclization reaction.
The facial selectivity of dioxa-cages and trioxa-cage is high selectivity.