Triscycloproparenes 1 and 2 were synthesized by treating the Diels-Alder adducts of 1-bromo-2-chlorocyclopropene and either hexaradialene (3) or hericene (4) with potassium t-butoxide. New cycloproparenes 5 and 6 were also isolated using this approach.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) The thermolysis of cyclopropa (b) naphthalene with C\sb60 was investigated and was found to yield a new Fullerene adduct. The biradical addition was also performed with \sp3He labeled Fullerene, and the product (7) was studied by \sp3He NMR.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) Silver (I) catalyzed reactions of several cycloproparenes were also investigated. In the absence of nucleophilic protic solvents or other reactants, benzocyclopropene (and its derivatives) could be dimerized to yield linearly fused six-membered rings as illustrated by the reaction of cycloproparene 8. Further aromatization of the dimers could be achieved (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) using DDQ in benzene. This technique was also employed with biscycloproparenes such as 11 and the new triscycloproparenes to obtain ladder polymers and more intricate nonrandomly cross-linked polymers.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)