- Versatile Method for the Simultaneous Synthesis of Two Ionic Liquids, Otherwise Difficult to Obtain, with High Atom Economy
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A new synthetic approach and full spectral (NMR, IR, MS) and ion chromatographic characterization (IC) of nitrogen-based ionic liquids bearing allyl- or ethyl- substituent and triflate, tosylate, methyl sulfate or methanesulfonate anion has been presented. On a sample of 16 new ionic liquids, the versatility of the anion exchange method has been proven. In the metathesis reactions that have been carried out, the halide anion was exchanged in ionic liquid with an alkyl sulfonate based anion using alkylating agents. The results obtained using ion chromatographic analysis on the newly synthesized compounds have been discussed. Also, the utilization of a gaseous methyl halide by-product, obtained in the metathesis reaction and otherwise difficult to synthesize, has been presented. This approach ensured high atom economy of the overall process, which makes the proposed methodology sustainable and eco-friendly.
- Szpecht, Andrea,Zajac, Adrian,Zielinski, Dawid,Maciejewski, Hieronim,Smiglak, Marcin
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p. 972 - 983
(2019/08/06)
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- Method of producing oxyborate Tetracyanobicyclo (by machine translation)
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PROBLEM TO BE SOLVED: To provide a method for efficiently producing a tetracyanoborate compound (VI). SOLUTION: A boron compound (for example, boron trichloride) and an ammonium derivative having a halogenide ion as a counter anion are mixed in xylol; then, a trialkylsilyl cyanide is added and reacted; the reaction system is subjected to a treatment with hydrogen peroxide, and an extraction treatment with butyl acetate; and butyl acetate is distilled out to obtain a tetracyanoborate compound represented by formula (VI) wherein [Kt]m+ is an ammonium cation; and m=1. In the formula, [Kt]m+ denotes an organic cation or an inorganic cation; and m denotes an integer of 1 to 3. COPYRIGHT: (C)2012,JPO&INPIT
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Paragraph 0075
(2016/12/26)
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- Alkylation of ammonium salts catalyzed by imidazolium-based ionic liquid catalysts
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Quaternary ammonium salts were synthesized from ammonium salts and dialkyl carbonates over imidazolium ionic liquid catalysts. The reaction gave almost stoichiometric amounts of the quaternary ammonium salts for halides and nitrates. It was found that the electron-donating property of the alkyl moieties of ammonium cations, the electrophilic nature of the alkyl group of the carbonate, the acidity of the acid that the anion of the ammonium salt corresponds to, and the steric hindrance of the ammonium salts and the dialkyl carbonates are the key factors that influence the yields of quaternary ammonium salts. Strong electron-donating alkyl groups on the nitrogen atom of the ammonium salt, electron-withdrawing groups on the methylene carbon of dialkyl carbonate, and weaker steric hindrance of the starting ammonium salts and dialkyl carbonates favor the alkylation reaction of ammonium salts.
- Zheng, Zhuo Qun,Wang, Jie,Wu, Ting Hua,Zhou, Xiao Ping
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p. 1095 - 1101
(2008/03/27)
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- Synthesis of bridgehead nitrogen heterocycles via cyclization of α- ammonio 5-hexenyl radicals
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Ring-closure of the 2,2-dimethyl-2-azonia-5-hexenyl radical (4) proceeds smoothly and efficiently to give the 5-exo isomer essentially quantitatively, in accordance with predictions based on MP4SDTQ/6-31G* ab initio calculations on the thermodynamic stability of α-ammonio radicals. The corresponding 5-hexynyl radical species 15 and its 6-phenyl derivative 19 display similar behavior affording the analogous 5-exo-3- methylenepyrrolidinium salts in high yield. In none of these cases were the products of reduction were detected. All of the radical intermediates were generated conveniently by treatment of the iodomethyl and/or phenylselenomethyl salts with tributyltin hydride. Application of this procedure to monocyclic precursors such as 1-methyl-1-iodomethyl-4-methylene- 1-azoniacyclohexyl iodide (31) provided an attractive entry into quaternary derivatives of the 1-azabicyclo[2.2.1]heptyl system in good yield via a three-step sequence from 1-methylpiperidone. Dequaternization of the bicyclic salts so obtained unexpectedly leads to rupture of one of the rings rather than loss of the N-methyl group. The 1-azabicyclo[2.2.1]heptane could be accessed readily via tin hydride-induced cyclization of the corresponding N- phenylethylammonium salt 54, followed by Hofmann elimination with potassium tert-butoxide.
- Della, Ernest W.,Smith, Paul A.
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p. 1798 - 1806
(2007/10/03)
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