| 研究生: |
吳傳益 Wu, Chuan-Yi |
|---|---|
| 論文名稱: |
6-甲氧基-1, 2, 3, 4-四苯基萘及
1-(4-甲氧基苯基)-2, 3, 4-三苯基萘之合成與討論 Synthesis and Discussion of 6-Methoxy-1, 2, 3, 4-Tetraphenylnaphthalene and 1-(4-Methoxyphenyl)-2, 3, 4-Triphenylnaphthalene |
| 指導教授: |
吳耀庭
Wu, Yao-Ting |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2011 |
| 畢業學年度: | 99 |
| 語文別: | 中文 |
| 論文頁數: | 38 |
| 中文關鍵詞: | 6-甲氧基-1, 2, 3, 4-四苯基萘 、1-(4-甲氧基苯基)-2, 3, 4-三苯基萘 |
| 外文關鍵詞: | 6-Methoxy-1, 2, 3, 4-Tetraphenylnaphthalene, 1-(4-Methoxyphenyl)-2, 3, 4-Triphenylnaphthalene |
| 相關次數: | 點閱:1167 下載:1 |
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多取代萘環在有機合成的領域中已發展多時,但在合成多取代萘環過程中所產生之異構物卻鮮少被人所討論。我們生成之異構物:6-甲氧基-1, 2, 3, 4-四苯基萘(26a)及1-(4-甲氧基苯基)-2, 3, 4-三苯基萘(26b),兩者間比例將隨著反應條件的不同而有所變異,其中較不對稱之異構物:1-(4-甲氧基苯基)-2, 3, 4-三苯基萘(26b),結構上因過去較少被討論,且該結構之合成也極少以單一步驟完成,故本人將於重點放此進行討論。
實驗中我們依序改變反應時的各種條件因素:反應溶劑、催化劑種類、磷化物種類及其與催化劑間的比例與用量、加熱時間、鹼的種類與用量。目的為了使1-(4-甲氧基苯基)-2, 3, 4-三苯基萘(26b)的相對比例能進行提升,甚至找出一組反應條件可以完全生成26b單一種產物結構。我們已找出以上條件因素之各別最佳化情形:THF當反應溶劑、催化劑為醋酸鈀而磷化物為參環己基磷且兩者間比例用量為5 mol%和15 mol%,所加入的鹼為醋酸銀0.5當量。但全部之有利因素集合起來結果卻沒太大改變,甚至比各別因素使用之效果還不如人意,藉此我們將更進一步探討提升26b結構之相關研究。
Highly substituted naphthalenes have been studied for a long times in organic synthesis chemistry, but the isomers produced in the synthesis process are rarely discussed. Different reaction conditions will result in different product ratio of highly substituted naphthalene isomer: 6-methoxy-1,2,3,4-tetraphenylnaphthalene (26a) and 1-(4-methoxyphenyl)-2,3,4-triphenylnaphthalene (26b). The structure of 1-(4-methoxyphenyl)-2,3,4-triphenylnaphthalene (26b) is rarely discussed and synthesized by one-step procedure, so main purpose we want of this research is to develop a simple synthetic method to get only one isomer(26b).
Different reaction condition such as solvent, catalyst, ligand, base and heating time were tested. The best condition is using THF, Pd(OAc)2 5 mol% / PCy3 15 mol%, 0.5eq AgOAc as base individually, but as we gather all the best condition there are not better then we think. In view of this, we will discussed more deeply about raising the ratio of 1-(4-methoxyphenyl)-2,3,4-triphenylnaphthalene(26b)
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