Crown Ether Assisted Chemical Reactions, II. Crown Ether Complexes of Potassium Phthalimide, Sodium Saccharinate and Sodium Acetylacetonate: New Reagents Containing Activated Anions

The synthesis of several crown ether and cryptand complexes with potassium phthalimide, sodium saccharinate and sodium acetylacetonate is reported. The anions in the complexes prove to be activated; this has been used to carry out a series of new nucleophilic substitutions with 2,4‐dinitrochlorobenzene, pentachloropyridine and pentafluoropyridine. Without addition of crown ethers these reactions could not be achieved. Only pentafluoropyridine reacts with potassium phthalimide alone, yielding a monosubstituted product. With crown ether assistance threefold substitution could be realized with pentafluoropyridine, whereas pentachloropyridine gave only monosubstitution.