Diethyl azodicarboxylate (DEAD)

Our Halloween 2012 series begins with a molecule that has the acronym DEAD. It stands for diethyl azodicarboxylate, an orange–red liquid that becomes yellow when diluted in a solvent. DEAD is a strong electron acceptor; it oxidizes iodide to molecular iodine, hydrazine to molecular nitrogen, alcohols to aldehydes, and thiols to disulfides. DEAD’s principal use is as a reagent in the Mitsunobu condensation reaction, and it participates in Michael and Diels–Alder reactions. Because it explodes when heated, it cannot be shipped in pure form. Instead, it is transported in solution or adsorbed onto plastic particles.