Synthesis of an Epoxide Carbonylation Catalyst: Exploration of Contemporary Chemistry for Advanced Undergraduates

Abstract

This lab presents an opportunity for advanced students of organic or inorganic chemistry to prepare a compound that belongs to a recently introduced class of catalyst that are active for the carbonylation of epoxides and related substrates to β-lactones and related products. Epoxides are inexpensive and readily available while β-lactones are not and have broad utility in both small molecule and polymer synthesis. Consequently, these catalysts, and related systems, have been the subject of intense investigation recently. The ability to work with a contemporary system was a major source of excitement and satisfaction to undergraduates at Cornell University who performed this experiment. The synthesis of the catalyst involves a simple organic reaction as well as two air-sensitive steps. The final step of the synthesis results in a dramatic color change and the resultant oxygen-sensitive compound may be characterized by IR, 1H-NMR, or X-ray crystallography.