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, f...

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Published inSynlett Vol. 25; no. 1; pp. 148 - 152
Main Authors Pugh, Coleen, Baker, James S., Storms, William K.
Format Journal Article
LanguageEnglish
Published Stuttgart · New York Georg Thieme Verlag 02.01.2014
Subjects
letter
Kumada coupling
benzyne
cycloaddition
benzocyclobutene
ring-opening isomerization
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0033-1339925