Cyclopropanes are interesting and useful structures in that they limit conformational flexibility without significantly changing a compound's electronics. Additionally, many N-heterocyclic compounds display important biological activity and are essential to the pharmaceutical industry. An intramolecular Kulinkovich cyclopropanation was used to make [3.1.0] and [4.1.0] azabicycles. Some of these compounds bear structural similarity to neurotransmitters, while others possess the pyrrolizidine core found in alkaloids with a myriad of therapeutic applications. The utility of the azabicycles is extended with a ring-expanding reaction. Although cyclopropylamines proved resistant to many types of reactions, it was found that the analogous cyclopropanols will undergo oxidative fragmentation. An intermolecular Kulinkovich reaction was used to make known and novel cycloproplyamines that are similar to histamine, tryptamine, mescaline and Ecstasy. These compounds were made in fewer steps than previous syntheses. Many of the known compounds are potent monoamine oxidase inhibitors and have potential in treating neurological disorders.