Resumen de Diastereospecific Synthesis of an Epoxide:: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry
Despite the prevalence of epoxide chemistry in the chemical literature and in all modern undergraduate organic textbooks, neither their reactions nor their preparation are common subjects of undergraduate organic lab experiments. This paper describes an operationally straightforward, two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" which probe the stereoselectivity of two important reactions: (i) halohydrin formation from alkenes and (ii) epoxide formation via intramolecular nucleophilic substitution. It complements the increasing number of puzzle-oriented undergraduate experiments combining synthesis and mechanistic discovery which continue to appear in this Journal.
