SYNTHESIS OF ALKYL AND ARYL 1-PROPENYL ETHER MONOMERS: A NEW APPROACH

Abstract

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 can be smoothly isomerized to the desired 1-propenyl ethers by refluxing in a basic ethanolic solution containing pentacarbonyliron as a catalyst. A simplified 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 reaction were investigated and a mechanism was proposed.

Keywords:

• Pentacarbonyliron
• Tetracarbonylhydroferrate (1-)
• Isomerization
• Allyl Ethers
• 1-Propenyl Ethers
• One-Pot Synthesis

ACKNOWLEDGEMENTS

The authors would like to gratefully acknowledge support of this work by the U.S. National Science Foundation and the Petroleum Research Fund administered by the American Chemical Society.