Organic Letters
Organic Letters
5 years ago

Synthesis, Characterization, and Reactivity of Thermally Stable Anhydrous Quaternary Ammonium Fluorides

Synthesis, Characterization, and Reactivity of Thermally Stable Anhydrous Quaternary Ammonium Fluorides
Nissan Ashkenazi, Yossi Zafrani, Ishay Columbus, Naama Karton-Lifshin, Lea Yehezkel, Shlomi Elias
The synthesis and properties of a new class of anhydrous quaternary ammonium fluorides, based on the rigid skeleton azabicyclo[2.2.2]octane, is described. Compounds 2a–d were easily prepared by passing the corresponding ammonium iodides over fluoride-based resin followed by drying their hydrated form at 100 or 140 °C under reduced pressure. The stability (experimental and theoretical study), solubility, reactivity, and characterization by solution and solid-state MAS NMR are discussed.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.6b03864

DOI: 10.1021/acs.orglett.6b03864

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