含氟烷基磺酰胺、含氟烷基磺酰亚胺的合成研究
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摘要
“超酸(super acid)”,是指酸性比100%浓硫酸还要强的酸性物质,它在化学合成和化学材料的应用中,有着非常高的实用价值。1923年,Conant首先使用“超酸”这词;1954年,Haszeldine和Kidd发现了三氟甲磺酸(TfOH)后超酸化学就迅速发展起来。在有机合成上,“超酸”主要用于稳定碳正离子,如R3C+等,和参与各种酸催化反应,作为新型锂电池固体电解质材料等。
全氟烷基磺酰亚胺(PFSI),即俗称的“全氟氮超酸”,是“超酸”的一种,是一类较强的Br?nsted酸。其配合物由于阴离子部分的结构特点,在一些Lewis酸参与的化学反应、高性能含氟材料的特殊用途等方面,表现出优异的性能,如全氟烷基磺酰亚胺金属盐能作为强Lewis酸,对许多有Lewis酸参与的机反应,起良好的催化作用;全氟烷基磺酰亚胺锂盐作为优良的新型锂电池含氟电解质材料;全氟烷基磺酰亚胺作为含氟离子液体前体等。
含氟化合物的化学性质往往难于预料,特别是全(多)氟化合物,碳链上多一个碳原子与少一个碳原子、含有杂原子和不含有杂原子、甚至在同一个位置上,有同族元素的不同原子作为官能团,这些物质在物理、化学性质上就可能就有很大的区别。为了拓展全氟烷基磺酰亚胺类氮超酸化合物的种类,并研究他们的性质,我们分别采用了一些长氟链的多氟烷基磺酰氟和短氟链的磺酰氯为原料,合成了一些全氟烷基磺酰亚胺及其衍生物。
本文以易得的5–碘–3–氧杂–八氟戊磺酰氟为原料,合成了5–碘–3–氧杂–八氟戊磺酰亚胺2及其衍生物(1,3,4,5,6,8,9,10,11),如5–氢–3–氧杂–八氟戊磺酰亚胺9、5–碘–3–氧杂–八氟戊磺酰亚胺钠盐10、5–碘–3–氧杂–八氟戊磺酰亚胺锂盐11等。在合成过程中,我们设计了五条合成5–碘–3–氧杂–八氟戊磺酰亚胺的路线,并对这些合成路线的优劣一一进行了比较,并进行了反应条件的优化摸索,选择最优的反应路线路线及条件进行合成。我们还以1–氯–2–碘四氟乙烷为原料,合成了2–氯–四氟乙磺酰胺及其衍生物,也尝试用多种方法合成1–氯–2–碘四氟乙磺酰亚胺,取得了一些有意义的结果。
本文探讨了5–碘–3–氧杂–八氟戊磺酰亚胺和1–氯–2–碘四氟乙磺酰亚胺的合成方法,为进一步拓展含氧杂原子的含氟烷基磺酰亚胺氮超酸的种类,为含氟离子液体、新型锂电池固体电解质材料等含氟材料的制备,提供了一定的合成基础。
“Superacids”, those stronger than 100% sulfuric acid, have been of great value to chemistry. In recent years, the bis(perfluoroalkanesulphon)amides complexes , which belong to superacid compounds, have been attracted great interest in development of science. They are widely used in organic synthesis as catalysts for Diels–Alder reaction and Friedel–Crafts reaction. Other applications were also found in ionic liquids and batteries. The abroad application of bis(perfluoroalksulphon)amides complexes results from the excellent property called as“Weakly-coordination”or“Noncoordination”.
Bis(ω–iodide–γ–oxy–octfluoropensulfony)amide is a special“superacid”.It might be hopefully modified to some multifunctional derivatives which can be used as ionic liquids and batteries etc. In attempt to find out the method of synthesis the special“superacids”and probe into the properties of them, bis(ω–iodide–γ–oxy–octfluoropensulfony)amide and some derivatives, such as bis(ω–hydro–γ–oxy–octfluoropensulfony)amide and so on, have been prepared fromω–fluorosulfonylperfluoroalkyl iodide .
In order to exploit more useful“superacids”, we have been attempted to prepare bis(2–chloro–tetra–fluoroethanesulfonyl)amid by 2–chloro–1,1,2,2–tetrafluoroethanesulfonyl chloride, and have get some achievement.
全氟烷基磺酰亚胺(PFSI),即俗称的“全氟氮超酸”,是“超酸”的一种,是一类较强的Br?nsted酸。其配合物由于阴离子部分的结构特点,在一些Lewis酸参与的化学反应、高性能含氟材料的特殊用途等方面,表现出优异的性能,如全氟烷基磺酰亚胺金属盐能作为强Lewis酸,对许多有Lewis酸参与的机反应,起良好的催化作用;全氟烷基磺酰亚胺锂盐作为优良的新型锂电池含氟电解质材料;全氟烷基磺酰亚胺作为含氟离子液体前体等。
含氟化合物的化学性质往往难于预料,特别是全(多)氟化合物,碳链上多一个碳原子与少一个碳原子、含有杂原子和不含有杂原子、甚至在同一个位置上,有同族元素的不同原子作为官能团,这些物质在物理、化学性质上就可能就有很大的区别。为了拓展全氟烷基磺酰亚胺类氮超酸化合物的种类,并研究他们的性质,我们分别采用了一些长氟链的多氟烷基磺酰氟和短氟链的磺酰氯为原料,合成了一些全氟烷基磺酰亚胺及其衍生物。
本文以易得的5–碘–3–氧杂–八氟戊磺酰氟为原料,合成了5–碘–3–氧杂–八氟戊磺酰亚胺2及其衍生物(1,3,4,5,6,8,9,10,11),如5–氢–3–氧杂–八氟戊磺酰亚胺9、5–碘–3–氧杂–八氟戊磺酰亚胺钠盐10、5–碘–3–氧杂–八氟戊磺酰亚胺锂盐11等。在合成过程中,我们设计了五条合成5–碘–3–氧杂–八氟戊磺酰亚胺的路线,并对这些合成路线的优劣一一进行了比较,并进行了反应条件的优化摸索,选择最优的反应路线路线及条件进行合成。我们还以1–氯–2–碘四氟乙烷为原料,合成了2–氯–四氟乙磺酰胺及其衍生物,也尝试用多种方法合成1–氯–2–碘四氟乙磺酰亚胺,取得了一些有意义的结果。
本文探讨了5–碘–3–氧杂–八氟戊磺酰亚胺和1–氯–2–碘四氟乙磺酰亚胺的合成方法,为进一步拓展含氧杂原子的含氟烷基磺酰亚胺氮超酸的种类,为含氟离子液体、新型锂电池固体电解质材料等含氟材料的制备,提供了一定的合成基础。
“Superacids”, those stronger than 100% sulfuric acid, have been of great value to chemistry. In recent years, the bis(perfluoroalkanesulphon)amides complexes , which belong to superacid compounds, have been attracted great interest in development of science. They are widely used in organic synthesis as catalysts for Diels–Alder reaction and Friedel–Crafts reaction. Other applications were also found in ionic liquids and batteries. The abroad application of bis(perfluoroalksulphon)amides complexes results from the excellent property called as“Weakly-coordination”or“Noncoordination”.
Bis(ω–iodide–γ–oxy–octfluoropensulfony)amide is a special“superacid”.It might be hopefully modified to some multifunctional derivatives which can be used as ionic liquids and batteries etc. In attempt to find out the method of synthesis the special“superacids”and probe into the properties of them, bis(ω–iodide–γ–oxy–octfluoropensulfony)amide and some derivatives, such as bis(ω–hydro–γ–oxy–octfluoropensulfony)amide and so on, have been prepared fromω–fluorosulfonylperfluoroalkyl iodide .
In order to exploit more useful“superacids”, we have been attempted to prepare bis(2–chloro–tetra–fluoroethanesulfonyl)amid by 2–chloro–1,1,2,2–tetrafluoroethanesulfonyl chloride, and have get some achievement.
引文
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2. P. J. F. de Rege, J. A. Gladysz, I. T. Horvath, Homopolyatomic cations of the elements[J]. Science. 1997, 276, 776.
3. P. J. Gillespie , J. Passmore, Spectroscopic observation of the formyl cation in a condensed phase[J]. Adv. Inorg. Chem. Radiochem. 1975, 17, 49.
4. T. A. O’Dommell, Superacids and Acidic Melts as Inorganic Chemical Reaction Media[M]. VCH, Weinheim, Germany, 1993.
5. H. Willner and F. Aubke, Homoleptic metal carbonyl cations of the electron–rich metals: Their generation in superacid media together with their spectroscopic and structural characterization[J]. Angew. Chem. Int. Ed. Engl. 1997, 36, 2402.
6. T. Drews and K. Seppelt, The Xe2+ Ion - Preparation and Structure[J]. Angew. Chem. Int. Ed. Engl. 1997, 36, 273.
7. I. Favier., E. Dunach. Novel electrosynthesis of metallic bis(trifluoromethanesulfonyl) imides[J]. Tetrahedron Lett. 2003, 44, 2032.
8. H. Strauss, The seatch for larger and more weakly coordinating anions[J]. Chem. Rev. 1993, 93, 927.
9. K. Seppelt, A Simple Route from Glucal to Cerny Epoxides[J]. Angew. Chem. Int. Ed. Engl. 1993, 32, 273.
10. A. Koppel, W. Taft, F. Anvia. The gas-phase acidities of very strong neutral bronsted acids[J]. J. Am. Chem. Soc. 1994, 116, 3047.
11. R. Arnaud, D. Benrabah, Theoretical study of CF3SO3Li, (CF3SO2)2NLi, and (CF3SO2)2CHLi ion pairs[J]. J. phys. Chem. 1996, 100,10882.
12. Li,X-Y, Nie, J, Density functional theory study on metal bis(trifluoromethylsulfonyl)imides: Electronic Structures, Energies, Catalysis, and Predictions[J]. J. phys. Chem. 2003, 107,6007.
13. 聂进,徐军,周光永,新型多氟氮超酸镧系金属盐的 Lewis 酸性研究[J]. 华中理工大学学报, 1999, 27,100.
14. Meubdoerffer, J. N, H. Niederprum. Bis(perfluoralkanesulfonyl)imides (RfSO2)2NH, Chem. Ztg. 1972, 96, 582.
15. J. Foropoulos, D. MesMarteau, Synthesis of perhaloalkanesulfonyl halides and their sulfonimide derivatives[J]. Inorg. Chem. 1993, 32, 5007.
16. Nie, J, Xu. J., Zhou, G-Y. , Lanthanide bis(trifluoromethylsulfonyl)amides as effective reusable catalysts for catalytic Friedel–Crafts acylation[J]. J. Chem. Res.,Synop.1999, 446.
17. Richard. D. Howells, Dellwood, William. M. Lamanna. Preparation of bis(fluoroalkylene- sulfonyl)imides and (fluoroalkylsulfony)(fluorosulfonyl)imides[P]. Patent, 1999, 587,4616.
18. Kensaku. Sogabe, Yasuchika. Hasegawa. Kensaku. Sogabe, Yasuchika. Hasegawa. A new one-pot synthesis bisperfluoroalkanesulfonylamides and bispentafluorobenzenesulfonyl- amide as potassium salts[J]. Chem. Lett. 2000, 944.
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