Akin to enamines, enol ethers are electron-rich alkenes by virtue of the electron-donation from the heteroatom via pi-bonding. Enol ethers have oxonium ion character. By virtue of their bonding situation, enol ethers display distinctive reactivity. In comparison with simple alkenes, enol ethers exhibit enhanced susceptibility to attack by electrophiles such as Bronsted acids. Similarly, they undergo inverse demand Diels-Alder reactions.
The reactivity of enol ethers is highly dependent on the presence of substituents alpha to oxygen. The vinyl ethers are susceptible to polymerization to give polyvinyl ethers. They also react readily with thiols in the thiol-ene reaction to form thioethers. This makes enol ether-functionalized monomers ideal for polymerization with thiol-based monomers to form thiol-ene networks.
Some vinyl ethers find some use as inhalation anesthetics. Enol ethers bearing α substituents do not polymerize readily. They are mainly of academic interest, e.g. as intermediates in the synthesis of more complex molecules.
The acid-catalyzed addition of hydrogen peroxide to vinyl ethers gives the hydroperoxide:
:CHOCH=CH  +  HO  →  CHOCH(OOH)CH