A Convenient Route to Tetraalkylammonium Perfluoroalkoxides from Hydrofluoroethers†
Benson J. Jelier
Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada)
Search for more papers by this authorDr. Jon L. Howell
Experimental Station, E. I. du Pont de Nemours, Wilmington, DE 19803 (USA)
Search for more papers by this authorProf. Craig D. Montgomery
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)
Search for more papers by this authorProf. Daniel B. Leznoff
Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada)
Search for more papers by this authorCorresponding Author
Prof. Chadron M. Friesen
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)Search for more papers by this authorBenson J. Jelier
Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada)
Search for more papers by this authorDr. Jon L. Howell
Experimental Station, E. I. du Pont de Nemours, Wilmington, DE 19803 (USA)
Search for more papers by this authorProf. Craig D. Montgomery
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)
Search for more papers by this authorProf. Daniel B. Leznoff
Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada)
Search for more papers by this authorCorresponding Author
Prof. Chadron M. Friesen
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)
Department of Chemistry, Trinity Western University, 7600 Glover Rd, Langley, B.C., V2Y 1Y1 (Canada)Search for more papers by this authorThe authors acknowledge funding from the Natural Sciences and Engineering Research Council of Canada (NSERC), Simon Fraser University (SFU), and Trinity Western University (TWU). In addition, we thank J. Ovens (SFU) for assistance with the structural determination of 6 a and A. Simonson (U of Utah) for assistance with TGA-MS.
Abstract
Hydrofluoroethers are shown to alkylate tertiary amines readily under solvent-free conditions, affording valuable tetraalkylammonium perfluoroalkoxides bearing α-fluorines. The reaction of RFCF2OCH3 (RF=CF2CF3, CF2CF2CF3, and CF(CF3)2) with NR1R2R3 produces twenty new α-perfluoroalkoxides, [(CH3)NR1R2R3][RFCF2O] under mild conditions. These α-perfluoroalkoxides are easy to handle, thermally stable, and can be used for the perfluoroalkoxylation of benzyl bromides.
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