Synthesis of a polymerizable benzocyclobutene that undergoes ring-opening isomerization at reduced temperature

Abstract

1-Ethoxyvinylbenzocyclobutene is a substituted benzocyclobutene that undergoes radical polymerization to produce polymers that can be crosslinked at 100-150 °C. The 4- and 5-vinyl isomers are synthesized in a 1:4 ratio via a halogenated benzyne intermediate produced from anthranilic acid, followed by cycloaddition with ethyl vinyl ether and replacement of the halogen atom with a vinyl group. © Georg Thieme Verlag Stuttgart · New York.