Synthesis of alkyl and aryl 1-propenyl ether monomers: A new approach

A new, convenient synthesis of alkyl and aryl 1-propenyl ether monomers in good to excellent yields has been developed. Alkyl and aryl allyl ethers ca n be smoothly isomerized to the desired 1-propenyl ethers by refluxing in a basic ethanolic solution containing pentacarbonyliron as a catalyst. A sim plified two-step, one-pot procedure has also been developed which consists of combining an alcohol with allyl bromide in the presence of base and then adding pentacarbonyliron to isomerize the in-situ generated allyl ether to directly give the 1-propenyl ether. Good yields of alkyl 1-propenyl ethers were obtained using this process. Factors affecting the isomerization reac tion were investigated and a mechanism was proposed.