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A Convenient Generation of Acetic Acid Dianion
Author(s) -
Parra Margarita,
Sotoca Enrique,
Gil Salvador
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390195
Subject(s) - chemistry , diethylamine , acetic acid , stoichiometry , lithium (medication) , octane , organic chemistry , amine gas treating , medicinal chemistry , medicine , endocrinology
The lithium enediolate of acetic acid can be generated efficiently, as a 0.5 M solution in THF, using lithium amides prepared from n ‐butyllithium in THF and either diethylamine or 1,3,3‐trimethyl‐6‐azabicyclo‐(3.2.1)‐octane (AZA). Its reaction with carbonyl compounds leads to the corresponding β‐hydroxy acids in good to moderate yields. Better yields are usually obtained when these amines are added in sub‐stoichiometric amounts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)