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研究生:陳冠蓁
論文名稱:茴香醛類似物之乙烯基氟化物合成
論文名稱(外文):The Synthesis of Vinyl Fluorides from Anisaldehyde Analogues
指導教授:黎世源黎世源引用關係
學位類別:碩士
校院名稱:文化大學
系所名稱:應用化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:1994
畢業學年度:82
語文別:中文
論文頁數:126
中文關鍵詞:茴香醛乙烯基氟化物
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本論文主要是研究箇香醛(anisaldehyde)類似物之乙烯基氮化物(vinyl fluorides)合成之探討。合成反應主要分為三個步驟,第一個步驟中,首先將diethyl phosphite和蒸餾過的苯甲醛(benzaldehyde)於甲醇鈉(sodium methoxide)鹼性溶液中進行反應,可得產物diethyl-α-hydroxybenzylphosphonate再將第一個步驟的重物與DAST(diethylaminosulfur trifluoride)進行反應,所得產物為dithyl-1-fluorobenzylphosphonate,係一種phosphonate ylide。最後利用Wadsworth-Emmons reaction 或稱Honer-Eemmons reaction, 將第二個步驟中產物diethyl-1-fluorobenzylphosphonate各與vanillin,isovanillin,3,4-dimethoxybenzaldehyde,2,4-dimethoxybenzaldehyde,2,5-dimethoxybenzalde,m-anisaldehy-六種含有醛基的反應物進行反應,分別得到FPHME1,FPHME2,FPME1,FPME2,FPME3,FPME等六種不乙烯基氟化物(vinyl fluorides)其之化學結構式之鑑定,則以19F-核磁共振光譜,1H-核磁共振光譜,13C-核磁共振光譜,質譜圖,紅外線光譜以及紫外線光譜等具體物理數據完成之。


The main purpose of this study is to investigate the synthesis of vinyl fluorides from anisaldehyde analogues. The synthetic reaction consists of three procedures. Firstly, diethyl phosphite which reacts with distilled benzaldehyde under alkaline solution of sodium methoxide gives a product of diethyl-α-hydro-xybenzyl phosphonate. Then,the product of the first procedure reacts with DAST(diethylamino-sulfur trifluoride) to give another product, diethyl-1-fluorobenzyl phosphonate. It is a kind of phosphonate ylide. Finally, diethyl-1-fluoro-benzyl phosphonate reacts with vanillin, isovanillin, 3,4-dimethoxybenzaldehyde, 2,4-dimethoxybenzaldehyde, 2,5-dimethoxybenzaldehyde, m-anisaldehyde which contain an aldehyde functional group, to obtain different vinyl fluoride products via the method of Wadsworth-Emmons reaction or so-called Horner-Emmons reaction. The products are represented as FPHME1, FPHME2, FPME1, FPME2, FPME3 and FPME, respectively. With regard to the identification of the products of vinyl fluorides, it was accomplished by means of 19F-NHR, 1H-NMR, 13C-NMR, MS, IR as well as UV spectra.

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