Cleavage of different ether bonds in butyl glycidyl ether and allyl glycidyl ether by K−, K+(15-crown-5)2

The kind of substituent in alkyl glycidyl ethers affects the course of their reaction with K−, K+(15-crown-5)2. The cyclic oxirane ring is exclusively cleaved in the case of butyl glycidyl ether whereas the presence of the unsaturated allyl group in the glycidyl ether molecule unexpectedly prefers the scission of the linear ether bond. In both the systems organometallic intermediates are formed. They react with crown ether causing its ring opening. Allylpotassium formed from allyl glycidyl ether reacts also with another glycidyl ether molecule; the oxirane ring is opened in this case.