Azodicarboxylic acid esters

In a 1-1., three-necked, round-bottomed flask equipped with a constant-pressure dropping funnel, a mechanical stirrer, and a reflux condenser is placed 174 g. (1.0 mole) of ethyl azodicarbox-ylate in 150 ml. of ether. Freshly prepared cyclopentadiene (70 g., 1.06 moles) is added dropwise over a 1-hour period to the stirred ethereal solution of diethyl azodicarboxylate. During the addition a gentle reflux is maintained by external cooling with an ice-water bath as needed. When the addition is complete, the reaction mixture is allowed to stand for 4 hours, or less if the yellow color of the azodicarboxylic acid ester disappears. I he dropping funnel and condenser are replaced by a glass stoj)pcr and a short distillation head, respectively. The ether and unreactcd diene are distilled off on a steam bath and the... 

Smissman, E.E., and Makriyannis, A. 1973. Azodicarboxylic acid esters as dealkylating agents. J Org Chem 38, 1652-1657. 

Huisgen, R., Pohl, H. Addition reactions of the N,N-double bond. III. The reaction of azodicarboxylic acid ester with olefins. Chem. Ber. 

Azodicarboxylic acid esters N,N -Diacyl-N,N -dialkoxy-hydrazines... 

Without additional reagents Azodicarboxylic acid ester adducts 1-Aminohydrazines from tert. amines... 

An interesting alternative in using diols, but starting from 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester (the same intermediate as used in the Gogte pathway above), was developed independently by the groups of Reynolds [25] and Bauerle [26], who utilized the Mitsunobu reaction with azodicarboxylic acid ester-phosphane as the etherification agent. 

Reactions of diazo with azo compounds a-Kctoaldehyde a/-dicarbalkoxyhydrazoncs from a-diazoketones and azodicarboxylic acid esters... 

Azodicarboxylic acid ester adducts Hydrazines by substituting addition... 

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