Synthesis of novel fluorous pyridinium ionic liquids

IF 1.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Mitsunori Honda, Kohei Ashizawa, Ko-Ki Kunimoto, Masahito Segi
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引用次数: 1

Abstract

The synthesis of a novel class of fluorous ionic liquids was investigated. The 2,6-diperfluoroalkyl-substituted pyridinium salts 2b-f were solids at ambient temperature and insoluble in perfluoromethylcyclohexane. The addition of much further fluorous alkyl group to nitrogen atom of 2,6-disubstituted pyridines 1 did not proceed to afford the pyridinium salts 3 having two or three perfluoroalkyl groups. On the other hand, the reaction of 3,5-diperfluoroalkyl-substituted pyridine 4 with perfluoroalkyl iodide proceeded to give N-perfluoroalkylpyridinium salts 6a and 7a in good yields. Furthermore, the addition of tris(perfluoroalkyl)silylpropyl iodide afforded the corresponding pyridinium salt 8a excellently. The anion exchange of the resulting iodides gave the ionic liquids with high fluorophilicity.

新型含氟吡啶离子液体的合成
研究了一类新型含氟离子液体的合成。2,6-二全氟烷基取代吡啶盐2b-f在室温下为固体,不溶于全氟甲基环己烷。在2,6-二取代吡啶1的氮原子上添加更多的氟烷基并不能得到具有两个或三个全氟烷基的吡啶盐3。另一方面,3,5-二氟烷基取代吡啶4与全氟烷基碘化物反应得到n -全氟烷基吡啶盐6a和7a,收率较高。此外,三(全氟烷基)硅丙基碘化物的加入也很好地提供了相应的吡啶盐8a。碘化物的阴离子交换使离子液体具有高亲氟性。
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来源期刊
Heteroatom Chemistry
Heteroatom Chemistry 化学-化学综合
CiteScore
1.20
自引率
0.00%
发文量
5
审稿时长
6 months
期刊介绍: Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.
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