The significance of nucleophilic substitution reactions in organic synthesis: Stereochemical models, mechanistic investigations, new synthetic methods

This thesis illuminates the contributing factors controlling nucleophilic substitution reactions of various analogues. Chapters two and three discuss the profound effect of heteroatom participation imparted by sulfur substituents on the reaction selectivity for cyclohexanone acetals and tetrahydropyran acetates. Electronic and steric effects of the heteroatom substituents govern the conformational preferences of the representative oxocarbenium ions. Chapter four highlights a novel approach to synthesizing a 1,2-dioxane endoperoxide utilizing an intramolecular allylic displacement cyclization. The synthesis and investigation of a model system is described.