Open AccessDirect Formation of the Carbonyl Anion of Diisopropyl Formamide
Author(s) -
Robert R. Fraser,
Patrick Hubert
Publication year - 1974
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v74-029
Subject(s) - chemistry , lithium diisopropylamide , formamide , benzaldehyde , propionaldehyde , ion , benzophenone , diisopropyl ether , butanone , acetone , photochemistry , organic chemistry , butyraldehyde , medicinal chemistry , aldehyde , deprotonation , catalysis , solvent
The reaction of diisopropyl formamide with lithium diisopropylamide produces, by abstraction of the formyl proton, the carbonyl anion, LiCON[CH(CH 3 ) 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.
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