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Diethyl azodicarboxylate acts as a dienophile used in Diels-Alder reactions. It is used as a reagent in alfa-thiocyanation of enolizable ketones with ammonium thiocyanate and annulation of N-protected imines. It acts as a reactant for the preparation of immunostimulants alfa-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 finds application in Mitsunobu reaction and used in the synthesis of pharmaceuticals like zidovudine and procarbazine. The presence of azo group in it is a Michael acceptor and used for the conversion of beta-ketoesters to the corresponding hydrazine derivatives in presence of copper(II) catalyst. Further, it is an efficient dehydrogenating agent, which is involved in the preparation of aldehydes, disulfides from alcohols and thiols respectively.
Explosion risk by heating undiluted material.
Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).
Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.
Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).
In combination with Triphenylphosphine, L02502 , is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild SN2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):
For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).
Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).
ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl azodicarboxylate, L19347 .
Wang, Y.; Frett, B.; McConnell, N.; Li, H. Y. Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media. Org. Biomol. Chem. 2015, 13 (10), 2958-2964.
Xu, N.; Li, D.; Zhang, Y.; Wang, L. Palladium-catalyzed direct ortho-ethoxycarbonylation of azobenzenes and azoxybenzenes with diethyl azodicarboxylate. Org. Biomol. Chem. 2015, 13 (34), 9083-9092.
Gefahrenhinweise (EU): H227-H302-H312-H315-H319-H335
Combustible liquid. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.