The Synthesis and Application of Polymer-Supported Hypervalent Iodine Reagent in the Organic Chemistry Laboratory

A project for an organic chemistry laboratory course for chemistry and biochemistry majors has been developed in which a polymer-supported hypervalent iodine reagent, IBX, was prepared in five linear steps and then used to oxidize 1° and 2° alcohols to aldehydes and ketones. Once used, the reduced polymer-supported product was recovered and regenerated, and analysis showed it to have a similar oxidative ability as the original polymer-supported IBX. In this experimental sequence, students applied a variety of important laboratory techniques, including TLC, flash chromatography, 1H NMR, FTIR, and GC-MS, and they ran reactions under an inert atmosphere. Moreover, students were exposed to a multistep synthesis, solid-state chemistry, and polymer-based chemistry. © 2010 American Chemical Society and Division of Chemical Education, Inc.