Abstract
The reactions of enol ethers (ROCC, R = alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl ethers. The ratio of these two products was highly dependent on the concentration of the reaction mixture. Thus, the selective formation of each product was conveniently attained by merely changing the amounts of the solvent used. Zinc iodide, a by-product of the reaction, plays a key role in the present cyclopropyl to allylic rearrangement. Ring-opened ionic intermediates are proposed.
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