4-Vinyl [2.2] paracyclophan (($) under bar 1) was successfully prepared as white crystals in 45 % yield via three step reactions. Monomer ($) under bar 1 was homopolymerizable with 2,2’-azobis(isobutyronitrile) (AIBN), boron trifluoride etherate, and butyllithium. Monomer ($) under bar 1 was copolymerizable with methyl acrylate and p-chlorostyrene in the presence of AIBN in benzene at 60 degrees C. It was found that monomer ($) under bar 1 was less conjugative and more electron-donating than styrene.