Potassium azodicarboxylate

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Potassium azodicarboxylate
Dipotassium azodicarboxylate.svg
Names
IUPAC name
Dipotassium N-carboxylatoiminocarbamate
Other names
Potassium azocarbonate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C2H2N2O4.2K/c5-1(6)3-4-2(7)8;;/h(H,5,6)(H,7,8);;/q;2*+1/p-2
    Key: UYKSYRMKGNNMMU-UHFFFAOYSA-L
  • C(=O)(N=NC(=O)[O-])[O-].[K+].[K+]
Properties
C2K2N2O4
Molar mass 194.229 g·mol−1
AppearanceYellow crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Potassium azodicarboxylate is a chemical compound with the formula C2K2N2O4. This chemical is used as a precursor to diimide. It can be synthesized by the reaction of potassium hydroxide with azodicarbonamide and it reacts with carboxylic acids to form diimide. [1]

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The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). Although DEAD and DIAD are most commonly used, there are a variety of other azodicarboxylates available which facilitate an easier workup and/or purification and in some cases, facilitate the use of more basic nucleophiles. It was discovered by Oyo Mitsunobu (1934–2003). In a typical protocol, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent, cool to 0 °C using an ice-bath, slowly add the DEAD dissolved in THF, then stir at room temperature for several hours. The alcohol reacts with the phosphine to create a good leaving group then undergoes an inversion of stereochemistry in classic SN2 fashion as the nucleophile displaces it. A common side-product is produced when the azodicarboxylate displaces the leaving group instead of the desired nucleophile. This happens if the nucleophile is not acidic enough or is not nucleophilic enough due to steric or electronic constraints. A variation of this reaction utilizing a nitrogen nucleophile is known as a Fukuyama–Mitsunobu.

<span class="mw-page-title-main">Diethyl azodicarboxylate</span> Chemical compound

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, 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.

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References

  1. Pasto, Daniel J. (2001). "Potassium Azodicarboxylate". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rp195. ISBN   9780470842898.