Direct electrophilic substitution of the cyclopentadienyl ring of cymantrene has been used to prepare five cymantrenyl-monomers with unsaturated sidechains. Direct substitution of cymantrene with acryloyl- and methacryloyl chloride under Friedel-Crafts conditions has led to acryloyl- and methacryloylcymantrene. The complexes have been characterized using 1H and 13C NMR, IR and elemental analysis. Both complexes polymerize under treatment with AIBN at 60–70°C. The chelated complex [n5-C5H4(CH2CH=CH2)]-Co[(NH)2C6H4], was prepared from the treatment of [n5-C5H4(CH2CH=CH2)]Co(CO)2 with I2 followed by (NH)2C6H4 and base. The complex was characterized with 1H NMR and IR but failed to undergo free-radical polymerization. The strategies used to prepare organometallic polymers are discussed.