Freeze-dried potassium fluoride was found to be much more effective as a hydrogen-bond forming catalytic reagent for alkylation of protic compounds than usual calcine-dried potassium fluoride. Phenol, thiophenol, aniline, and acetylacetone were easily alkylated with methyl or ethyl iodide in the presence of the reagent. Freeze-dried potassium fluoride, however, had no effect for the fluorination of activated chlorine compounds.
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Ishikawa et al. (1980) studied this question.