The (2.2) paracyclophane-annelated cycloproparenes 1 and 2 were prepared by treating the Diels-Alder adducts of 1-bromo-chlorocyclopropene and either 1-vinyl (2.2) paracyclophane-1-ene (3) or 1,2-dimethylene (2.2) paracyclophane (4) with potassium t-butoxide in THF. Using the same approach the new cycloproparenes 5 and 6 were obtained from the (2.2) paracyclophanetetraenes 7 and 8.* The silver-ion catalyzed polymerization of the dicycloproparenes 9 and 10 was also studied. This method has shown to be an alternative to the repetitive Diels-Alder reaction in the synthesis of ladder polymers. The ladder polymers 11 and 12 were obtained and characterized by IR, solid-state \sp13C-NMR and thermogravimetric analysis (TGA).* ftn*Please refer to the dissertation for diagrams.