A facile and efficient synthesis of new fluoroalkylsulfonates and the corresponding tetrabutylammonium salts |
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| Institution: | 1. Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Chemical and Environmental Engineering, Jianghan University, Wuhan 430056, Hubei, PR China;2. Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, Shandong, PR China;1. Department of Chemistry, University College of Science, University of Calcutta, 92, A.P.C. Road, Kolkata 700009, India;2. Department of Chemistry, Jadavpur University, Jadavpur, Kolkata 700032, India;3. Department of Chemistry, Darjeeling Govt. College, Darjeeling 734101, India;4. Department of Chemistry, Serampore College, Serampore, Hooghly 712201, India;5. Departament de Química Inorgànica, Universitat de Barcelona Martí i Franquès, 1-11, 08028 Barcelona, Spain;1. Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain;2. X-ray-Diffraction Service from Nucleus, Plaza de los Caídos 1-5, 37008 Salamanca, Spain;1. Missouri University of Science and Technology, United States;2. Australian College of Kuwait, Kuwait;3. Oklahoma State University, United States;1. Department of Chemistry, Indiana University, Bloomington, IN 47405, USA;2. Eastman Chemical Company, Kingsport, TN 37664, USA;3. Department of Chemistry, The University of Jordan, Amman 11942, Jordan;4. Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA;1. School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China;2. Department of Chemical Engineering and Applied Chemistry, University of Toronto, Toronto, ON, Canada M5S 3E5;3. Department of Chemical and Biochemical Engineering, Western University, London, ON, Canada N6A 5B9 |
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| Abstract: | A useful synthetic methodology towards new fluoroalkylsulfonates was developed. Grignard addition to an inexpensive and commercially available fluorine-containing ester, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (1) gave the mono-adduct (2) as the only product in high yield. The scope and limitation of this method were thoroughly investigated and it was found that it works for most Grignard reagents except electron-poor ones. Interestingly, the resulting fluoroalkylsulfonates exhibit substituent-dependent hydration behavior due to the presence of carbonyl group in these compounds. Converting the fluoroalkylsulfonate to the acid form and then neutralizing it with tetra-n-butylammonium hydroxide gave the corresponding tetra-n-butylammonium salts, which shows good solubility in common organic solvents, some of which might be suitable for copolymerization with other hydrophobic monomers. |
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| Keywords: | Grignard reagents Methyl 2 2-difluoro-2-(fluorosulfonyl)acetate Fluoroalkylsulfonate Quaternary ammonium sulfonate compounds |
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