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A convenient route to tetraalkylammonium perfluoroalkoxides from hydrofluoroethers
Benson J Jelier1, Jon L Howell, Craig D Montgomery
1Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada).
Abstract:
Hydrofluoroethers are shown to alkylate tertiary amines readily under solvent-free conditions, affording valuable tetraalkylammonium perfluoroalkoxides bearing α-fluorines. The reaction of R(F)CF2-OCH3 (R(F)=CF2CF3, CF2CF2CF3, and CF(CF3)2) with NR(1)R(2)R(3) produces twenty new α-perfluoroalkoxides, [(CH3)NR(1)R(2)R(3)][R(F)CF2O] 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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