Cyclic aryl ether oligomers containing the trans-1,2-diphenylcyclopropane moiety were synthesized in high yield from 1,2-bis(p-hydroxyphenyl)cyclopropane and 1-(3-hydroxyphenyl)-2-(4’-hydroxyphenyl) propane by reaction with 1,2-bis(4-fluorobenzoyl)benzene or 1,2-di(4-fluorobenzoyl)-3,6-diphenylbenze. These oligomers undergo melt polymerization readily to give a crosslinked polymer in the presence of a phenolate salt as catalyst. The cyclic oligomers were characterized utilizing gel permeation chromatography, nuclear magnetic resonance and matrix-assisted laser desorption ionization mass spectrometry. Thermal analysis was conducted by differential scanning calorimetry and thermogravimetric analysis.