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Diethyl azodicarboxylate
Diethyl azodicarboxylate, often abbreviated DEAD, is the organic compound CH3CH2O2CN=NCO2CH2CH3. As indicated with this formula, the molecule consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This red orange liquid is a valuable reagent but also quite dangerous. Additional recommended knowledge
PreparationAlthough widely available, diethyl azodicarboxylate can be prepared in the laboratory. A two-step synthesis starts from hydrazine, first by alkylation with ethyl chloroformate. followed by treating the resulting ethyl hydrazodicarboxylate with chlorine.[1]
Red fuming nitric acid can also be used in the second step.[2] ApplicationsDEAD is an efficient component in Diels-Alder reactions and in click chemistry, for example the synthesis of Bicyclo[2.1.0]pentane, which originates from Otto Diels.[3] DEAD is an important reagent in the Mitsunobu reaction where it forms an adduct with phosphines. In one study[4] the compound together with triphenylphosphine and a chalcone formed a pyrazoline: SafetyDEAD is toxic, shock sensitive, and thermally unstable. It is handled as a solution, rarely as the pure compound. This safety hazards have resulted in DEAD usage rapidly declining and being replaced with DIAD (Diisopropyl azo dicarboxylate). References
Categories: Diazo compounds | Reagents for organic chemistry |
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diethyl_azodicarboxylate". A list of authors is available in Wikipedia. |