Ivanov reaction

The Ivanov reaction is the chemical reaction of the dianions (endiolates) of aryl acetic acids (Ivanov reagents) with electrophiles, primarily carbonyl compounds or isocyanates. The reaction was named after the Bulgarian organic chemist, Academician Dimitar Ivanov, who discovered it.



Ivanov reagents (dianions of aryl acetic acids) react with many electrophiles, including aldehydes, ketones, isocyanates, and alkyl halides. The product does not usually spontaneously decarboxylate, but it is possible with some reagents. Use of the dianion of phenylacetic acid with formaldehyde gives tropic acid, an intermediate used in the synthesis of atropine and hyoscyamine.

The Ivanov reaction is known to proceed through the Zimmerman-Traxler model transition state. Toulec et al. have investigated the reaction rates and kinetics.