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.[1][2][3][4] The reaction was named after the Bulgarian organic chemist, Academician Dimitar Ivanov, who discovered it.
![The Ivanov reaction](http://upload.wikimedia.org/wikipedia/commons/5/55/Ivanov_Reaction.gif)
Ivanov reagents (dianions of aryl acetic acids) react with many electrophiles, including aldehydes, ketones, isocyanates, and alkyl halides.[5] The product does not usually spontaneously decarboxylate, but it is possible with some reagents.
The Ivanov reaction is known to proceed through the Zimmerman-Traxler model transition state[6]. Toulec et al. have investigated the reaction rates and kinetics.[7]
See also[edit]
References[edit]
- ^ Ivanov, D.; Spassoff, A. Bull. Soc. Chim. France 1931, 49, 19 & 375.
- ^ Ivanov, D. et al. Bull. Soc. Chim. France 1932, 51, 1321 & 1325 & 1331.
- ^ Blagoev, B.; Ivanov, D. Synthesis 1970, 615–627. (Review)
- ^ Ivanov, D. Synthesis 1975, 83–98. (Review)
- ^ Hauser, C. R.; Dunnavant, W. R. (1960). "α,β-Diphenylpropionic acid". Organic Syntheses. 40: 38. doi:10.15227/orgsyn.040.0038.
- ^ Zimmerman, H. E.; Traxler, M. D. (1957). "The Stereochemistry of the Ivanov and Reformatsky Reactions". Journal of the American Chemical Society. 79 (8): 1920–1923. doi:10.1021/ja01565a041.
- ^ Toullec, J.; Mladenova, M.; Gaudemar-Bardone, F.; Blagoev, B. J. Org. Chem. 1985, 50, 2563.