Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT,[6][7] is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.
DEAD is an aza-dienophile and an efficient dehydrogenating agent, converting alcohols to aldehydes, thiols to disulfides and hydrazo groups to azo groups; it is also a good electron acceptor. While DEAD is used in numerous chemical reactions 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.[8] It is used in the synthesis of various natural products and pharmaceuticals such as zidovudine, an AIDS drug; FdUMP, a potent antitumor agent; and procarbazine, a chemotherapy drug.
^Diethyl azodiformate. Webbook.nist.gov (1972-07-28). Retrieved on 2011-03-15.
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^L19348 Diethyl azodicarboxylate, 97% – Alfa Aesar – A Johnson Matthey Company. Alfa.com (1972-07-28). Retrieved on 2011-03-15.
^Caroline Cooper (23 July 2010). Organic Chemist's Desk Reference. CRC Press. pp. 109–. ISBN 978-1-4398-1164-1. Retrieved 12 March 2011.
^DEAD is sometimes used for another chemical, diethyl acetylenedicarboxylate. P. N. Preston (1980). Benzimidazoles and congeneric tricyclic compounds. John Wiley and Sons. pp. 475–. ISBN 978-0-471-08189-0. Retrieved 12 March 2011.
^Barbara., Czakó (2009). Strategic applications of named reactions in organic synthesis: background and detailed mechanisms ; 250 named reactions. Elsevier. ISBN 978-0-12-369483-6. OCLC 634820219.
and 16 Related for: Diethyl azodicarboxylate information
(2004). "Aza-Baylis–Hillman reactions of diisopropyl azodicarboxylate or diethylazodicarboxylate with acrylates and acrylonitrile". Tetrahedron. 60 (9):...
using triphenylphosphine and an azodicarboxylate such as diethylazodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). Although DEAD and DIAD...
also been used as a reagent in the Mitsunobu reaction in place of diethylazodicarboxylate. Tetsuto Tsunoda, Hiroto Kaku, N,N,N′,N′-Tetramethylazodicarboxamide...
treated with 2-hydroxytetrahydropyranyl, triphenylphosphine, and diethylazodicarboxylate (DEAD) in tetrahydrofuran (THF). Commonly, THP ethers are deprotected...
air. N2H4 + H2O2 → N2H2 + 2H2O Alternatively the hydrolysis of diethylazodicarboxylate or azodicarbonamide affords diimide: Et−O2C−N=N−CO2−Et → HN=NH...
of dead animal tissue. DEAD, DEADCAT Diethylazodicarboxylate: An apt acronym, given that diethylazodicarboxylate is explosive; shock sensitive; carcinogenic;...
arenesulfonylhydrazine in the presence of triphenylphosphine and diethylazodicarboxylate. Unlike hydrazone-synthesis reactions, this reaction occurs on...
The molecular formula C6H10N2O4 may refer to: Diethylazodicarboxylate Formiminoglutamic acid This set index page lists chemical structure articles associated...
diene reactions, including with dienophiles dimethylmesoxalate, diethylazodicarboxylate. In the process, Achmatowicz and his co-workers — F. Werner-Zamojska...
example, the ene reaction of cyclopentene and cyclohexene with diethylazodicarboxylate can be catalyzed by free-radical initiators. As seen in Figure...
reaction, a mixture of triphenylphosphine and diisopropyl azodicarboxylate ("DIAD", or its diethyl analogue, DEAD) converts an alcohol and a carboxylic acid...
ortho-nitrobenzenesulfonylhydrazine in the presence of triphenylphosphine and diethylazodicarboxylate. Unlike hydrazone-synthesis reactions, this reaction occurs on...
group to an amine in 60 was a Mitsunobu reaction (hydrogen azide, diethylazodicarboxylate, triphenylphosphine with azide reduction to amine by Ph3P). The...
Phosphoric Acid by the Reaction of Trivalent Phosphorus Compounds with DiethylAzodicarboxylate in the Presence of Alcohols". Bull. Chem. Soc. Jpn. 40 (4): 935–939...
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