Diethyl azodicarboxylate

Reagent for synthesis. Diethyl azodicarboxylate acts as a dienophile used in Diels-Alder reactions. It is used as a reagent in α-thiocyanation of enolizable ketones with ammonium thiocyanate and annulation of N-protected imines. It acts as a reactant for the preparation of immunostimulants α-Galactosylceramides, bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase and aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes. It is a commonly used activating reagent in Mitsunobu reaction and used in the synthesis of pharmaceuticals like zidovudine and procarbazine. In addition, it is an efficient dehydrogenating agent, which is involved in the preparation of aldehydes, disulfides, hydrazo groups from alcohols, thiols and azo goups, respectively. It is also a good electron acceptor. It is mostly known as a key component of the Mitsunobu reaction, a common strategy for the preparation of an amine, azide, ether, thioether or ester from the corresponding alcohol.