title: A convenient route to tetraalkylammonium perfluoroalkoxides from hydrofluoroethers.
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.
authors.affiliation: Dept of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6 (Canada).
authors.forename: Benson J
authors.initials: BJ
authors.lastname: Jelier
authors.forename: Jon L
authors.initials: JL
authors.lastname: Howell
authors.forename: Craig D
authors.initials: CD
authors.lastname: Montgomery
authors.forename: Daniel B
authors.initials: DB
authors.lastname: Leznoff
authors.forename: Chadron M
authors.initials: CM
authors.lastname: Friesen
mesh_terms: D000478:Alkylation; D064751:Ammonium Compounds / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*
chemical_list: D064751:Ammonium Compounds; D004987:Ethers; D005461:Fluorine
keywords: alkylation; fluorine; hydrofluoroether; perfluoroalkoxide; reactive intermediates