Hydrazone formation

Hydrazone Formation Mechanism

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Reaction of carbonyl with hydrazine gives a hydrazone. Hydrazine is more nucleophilic than a regular amine due to a presence of the adjacent nitrogen. Note the similarity to the formation of an oxime reaction. Hydrazones generally form a mixture of geometric isomers.

J. M. Sayer, B. Pinsky, A. Schonbrunn and W. Washtien, J. Am. Chem. Soc., 1974, 96, 7998–8009.


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