Unexpected Cleavage of Crown Ether in the Reaction of Methyloxirane with K-,K+(15-crown-5)2

Cleavage of oxirane and crown ether rings occurs when the supramolecular complex K-,K+(15-crown-5)2 reacts with methyloxirane in tetrahydrofuran solution. Potassium isopropoxide and potassium tetraethylene glycoxide vinyl ether are the main products of the reaction. The cleavage of 15-crown-5 is observed also in the reaction of the metal complex with methyl iodide. That means that the crown ether acts both as an activator and as a reagent in these processes. The solvent was inert in the studied systems.