氣態一氯三氟乙烯在有機合成上的應用
碩士 === 國防大學中正理工學院 === 應用化學研究所 === 95 === Bromotrifluoroethene (F2C=CFBr) is expensive, and it is not allowed to be imported into Taiwan. Base on this situation, this research used the gasous chlorotrifluoroethene (F2C=CFCl) instead of bromotrifluoroethene as starting material to carry out the organi...
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ndltd-TW-095CCIT05000122016-05-25T04:14:20Z http://ndltd.ncl.edu.tw/handle/62354275819988791083 氣態一氯三氟乙烯在有機合成上的應用 Te-Chuan,Chou 周德全 碩士 國防大學中正理工學院 應用化學研究所 95 Bromotrifluoroethene (F2C=CFBr) is expensive, and it is not allowed to be imported into Taiwan. Base on this situation, this research used the gasous chlorotrifluoroethene (F2C=CFCl) instead of bromotrifluoroethene as starting material to carry out the organic synthetic work. Treatment of chlorotrifluoroethene with n-butyllithium (n-BuLi) gave salt of [F2C=CF]-Li+ which underwent the silylation with chlorodimethylphenylsilane (PhMe2SiCl), trimethylsilyl chloride (Me3SiCl) and triethylsilyl chloride (Et3SiCl) to afford dimethylphenylsilyl trifluoroethylene (F2C=CFSiMe2Ph), trimethylsilyltrifluoroethylene (F2C=CFSiMe3) and triethyls ilyltrifluoroethylene. (F2C=CFSiEt3), respectively. In the presene of potassium fluoride and dimethylformamide (DMF) as solvent, reaction of the silylated compounds F2C=CFSiR3 with tributyltinchloride (Bu3SnCl) provided the tributyltintrifluoroethene (F2C=CFSnBu3) compound. Substitation of tributyltin group with iodine was carried out under a flash distillation to achieve the iodotrifluoroethene (F2C=CFI) which the boiling point is 30 oC. The total yields from chlorotrifluoroethene to iodotrifluoroethene was 58 %. This reseach also used chlorotrifluoroethene as a starting material to prepare the phosphono-containing compound fluorocarbethoxymethylphosphonate ((EtO)2P(O) CFHCO2Et), Treatment of chlorotrifluoroethene with sodium ethoxide gave 1- ethoxy-1,1,2-trifluoro-2-chloroethene (CFHClCF2OEt) with sequently converted the CF2 group into carbonyl group under sulfuric acid to achieve ethyl chloro fluoroacetate CFHClCO2Et. Finally, the fluoro-containing phosphonate (EtO)2 P(O)CFHCO2Et was synthesized via Michaelis-Arbuzov reaction by reaction of triethylphosphite (EtO)3P with CFHClCO2Et. The total yield from chlorotri fluoroethene to (EtO)2P(O)CFHCO2Et was 56 %. The Nuclear Magnetic Resonance (1H、13C、19F、31P NMR), Mass spectrometer and Fourier Transform Infared Spectrometer (FTIR) spectra were used to identify the structure of the compounds. 蔡厚仁 2007 學位論文 ; thesis 0 zh-TW |
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碩士 === 國防大學中正理工學院 === 應用化學研究所 === 95 === Bromotrifluoroethene (F2C=CFBr) is expensive, and it is not allowed to be imported into Taiwan. Base on this situation, this research used the gasous chlorotrifluoroethene (F2C=CFCl) instead of bromotrifluoroethene as starting material to carry out the organic synthetic work. Treatment of chlorotrifluoroethene with n-butyllithium (n-BuLi) gave salt of [F2C=CF]-Li+ which underwent the silylation with chlorodimethylphenylsilane (PhMe2SiCl), trimethylsilyl chloride (Me3SiCl) and triethylsilyl chloride (Et3SiCl) to afford dimethylphenylsilyl trifluoroethylene (F2C=CFSiMe2Ph), trimethylsilyltrifluoroethylene (F2C=CFSiMe3) and triethyls ilyltrifluoroethylene. (F2C=CFSiEt3), respectively. In the presene of potassium fluoride and dimethylformamide (DMF) as solvent, reaction of the silylated compounds F2C=CFSiR3 with tributyltinchloride (Bu3SnCl) provided the tributyltintrifluoroethene (F2C=CFSnBu3) compound. Substitation of tributyltin group with iodine was carried out under a flash distillation to achieve the iodotrifluoroethene (F2C=CFI) which the boiling point is 30 oC. The total yields from chlorotrifluoroethene to iodotrifluoroethene was 58 %.
This reseach also used chlorotrifluoroethene as a starting material to prepare the phosphono-containing compound fluorocarbethoxymethylphosphonate ((EtO)2P(O) CFHCO2Et), Treatment of chlorotrifluoroethene with sodium ethoxide gave 1- ethoxy-1,1,2-trifluoro-2-chloroethene (CFHClCF2OEt) with sequently converted the CF2 group into carbonyl group under sulfuric acid to achieve ethyl chloro fluoroacetate CFHClCO2Et. Finally, the fluoro-containing phosphonate (EtO)2 P(O)CFHCO2Et was synthesized via Michaelis-Arbuzov reaction by reaction of triethylphosphite (EtO)3P with CFHClCO2Et. The total yield from chlorotri fluoroethene to (EtO)2P(O)CFHCO2Et was 56 %. The Nuclear Magnetic Resonance (1H、13C、19F、31P NMR), Mass spectrometer and Fourier Transform Infared Spectrometer (FTIR) spectra were used to identify the structure of the compounds.
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author2 |
蔡厚仁 |
author_facet |
蔡厚仁 Te-Chuan,Chou 周德全 |
author |
Te-Chuan,Chou 周德全 |
spellingShingle |
Te-Chuan,Chou 周德全 氣態一氯三氟乙烯在有機合成上的應用 |
author_sort |
Te-Chuan,Chou |
title |
氣態一氯三氟乙烯在有機合成上的應用 |
title_short |
氣態一氯三氟乙烯在有機合成上的應用 |
title_full |
氣態一氯三氟乙烯在有機合成上的應用 |
title_fullStr |
氣態一氯三氟乙烯在有機合成上的應用 |
title_full_unstemmed |
氣態一氯三氟乙烯在有機合成上的應用 |
title_sort |
氣態一氯三氟乙烯在有機合成上的應用 |
publishDate |
2007 |
url |
http://ndltd.ncl.edu.tw/handle/62354275819988791083 |
work_keys_str_mv |
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