Hazardous Chemistry: Azodicarboxylic Acid Derivatives

Azodicarboxylic acid derivatives

At large scale, we produce azodicarboxylic acid derivatives which are predominantly used in the Mitsunobu Reaction. This reaction provides a formal dehydration under very mild conditions by stereospecific substitution of hydroxyl groups with a broad variety of nucleophiles using mixtures of azodicarboxylic esters or amides, in combination with triphenylphosphine (TPP) or phosphites.

Mitsunobu Reaction

With the Mitsunobu Reaction intermolecular substitution leads to esters, ethers, thioethers and isothiocyanates. Via the intramolecular variant lactones and lactames can be obtained.

Alternative Mitsunobu Reagents:

Several other azo compounds have been developed as alternatives to DIAD, e.g.:

Dibenzyl azodicarboxylate, DBAD	Azodicarbonyldipiperidide ADDP	N,N,N´,N´-Tetramethyl azodicarbonamide, TMAD

 

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