Leading Question: Why Do We Use PIDA? (not to be confused with pita- a Mediterranean staple food)

(Diacetoxyiodo)benzene was first synthesized by Conrad Willgerodt (1841-1930), a german chemist credited with discovery of the Willgerodt reaction. This compound, also known simply as PIDA, is the result of a reaction between iodosobenzene, also synthesized first by Willgerodt, and acetic acid.

PIDA is most widely used as an oxidizing agent but can also be used in some substitution reactions, such as the substitution of acetate groups to create a reagent for the Hofmann rearrangement. The Hypervalent Iodine in PIDA, as an electron deficient atom, can be attacked by a hydroxyl oxygen. Nucleophilic attack, or another reaction with similar results, can then be facilitated to create a protonated carbonyl, after the remnants of PIDA have left. Deprotonation is all that is then needed to completely oxidize the molecule.

(Diacetoxyiodo)benzene is favorable to other oxidizing agents because it is a compound absent of toxic heavy-metals, in contrast to Chromium Oxide used in oxidation with Jones’ reagent for example. With the increasing importance of environmental health over the past 50 years, finding and using reagents that are more friendly to the environment is important to scientists, especially if they want to get into The Good Place.