Thesis advisor: Marc L. Snapper / Intramolecular [2+2] photocycloadditions have been studied: (i) Previous studies in our group have demonstrated that there is a regiochemical dependence of intramolecular [2+2] photocycloadditions on the solvent employed. In order to understand the generality of hydrogen bonding effects of photochemical reactions of β-hydroxyl enones, we examined the photochemical outcome of enones with both acyclic and cyclic olefin tethers. (ii) An application of an intramolecular [2+2] photocycloaddition/ fragmentation strategy to form 5-8-5 ring systems has been demonstrated toward the synthesis of the natural product cycloaraneosene. / Thesis (PhD) — Boston College, 2008. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.