Easy Conversion of Dimethyl α-(Bromomethyl)fumarate into Functionalized Allyl Ethers Mediated by DABCO

Abstract

New functionalized allyl ethers were obtained in good yields following the mild selective reaction of different alcohols with allyl bromide in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) and a catalytic amount of triethylamine (TEA) at room temperature.

GRAPHICAL ABSTRACT

Keywords:

• Alcohols
• DABCO
• dimethyl α-(bromomethyl)fumarate
• functionalized allyl ethers
• trimethylamine

ACKNOWLEDGMENTS

The authors thank Jacques Lebreton (Nantes University in France) for the HRMS analysis and M. A. Sanhoury, MRSC, from the Faculty of Science of Tunis (Tunisia) for helpful discussions.

SUPPLEMENTAL MATERIAL

Complete experimental procedure and relevant spectra (¹H, ¹³C NMR, IR, and HRMS spectra) for compounds 3a–i can be accessed on the publisher’s website.