The synthesis and polymerization of dicycloproparenes
Harmon, Brenda Bacon
Master of Arts
Dicycloproparenes 1 and 2 were synthesized by treating the Diels-Alder adducts of 1-bromo-2-chlorocyclopropene and either 2,3,5,6-tetramethylidene-bicyclo[2.2.2]octane (3) or 1,2,4,5-tetramethylenecyclohexane (4) with potassium t-butoxide in tetrahydrofuran.* The silver catalyzed polymerization of each dicycloproparene was investigated. The dimers 5a and 5b were observed and isolated at an early stage during the polymerization of dicycloproparene 1.* The ladder polymer formed by treating the linearly fused dicyclopropanthracene 2 with silver ion in chloroform was characterized by solid state nuclear magnetic resonance spectroscopy. The insoluble dimer of 2 could not be isolated.* *Please refer to dissertation for diagrams.