Chairperson, Graduate Committee: Matthew CookCasey, Aoife2022-04-222022-04-222021https://scholarworks.montana.edu/handle/1/16345Cyclopentanes and cyclopentenes are present in many natural products and pharmaceuticals. Despite their presence in many natural products and pharmaceuticals there are few general methods to synthesize highly functionalized 5-membered carbocycles. Using substituted allyl vinyl ethers, highly functionalized 5-membered carbocycles can be accessed through a Claisen rearrangement followed by an intramolecular Sakurai reaction. Due to the acid sensitive nature of these allyl vinyl ethers, Lewis acid catalysis is not a viable reaction pathway but the use of H-bond donors as organocatalysts is an attractive method to develop a synthetic methodology to access 5-membered carbocycles. Through NMR and computational studies, the activation parameters of a these HBD catalyzed Claisen rearrangement has been studied and further knowledge into the mechanism of these reaction pathways has been gained.enOrganic compoundsCatalystsEthersRearrangements (Chemistry)AcidsDissertationCopyright 2021 by Aoife Casey