Direct Formation of the Carbonyl Anion of Diisopropyl Formamide
- 1 January 1974
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 52 (1) , 185-187
- https://doi.org/10.1139/v74-029
Abstract
The reaction of diisopropyl formamide with lithium diisopropylamide produces, by abstraction of the formyl proton, the carbonyl anion, LiCON[CH(CH3)2]2. Reactions of this anion with benzaldehyde, benzophenone, ethyl benzoate, acetone, and propionaldehyde occur in yields ranging from 30–92%. Thus, this anion provides a useful method for the synthesis of α-hydroxy and α-keto acids, particularly in cases where cyanohydrin formation is difficult.Keywords
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