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Über die Wanderung der Carboxylatgruppe bei der Benzilsäureumlagerung. 26. Mitteilung über Reduktone und Tricarbonylverbindungen
Author(s) -
RodéGowal Heike,
Dahn Hans
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560631
Subject(s) - chemistry , hydrolysis , carboxylate , alkaline hydrolysis , medicinal chemistry , solvolysis , group (periodic table) , butyrate , nuclear chemistry , organic chemistry , fermentation
The benzilic acid rearrangement of ethyl α,β‐dioxo‐butyrate was studied by NMR.‐and UV.‐techniques. In weak alkaline media (pH < 10) the ester group is hydrolyzed first, then the carboxylate group migrates to form methyltartronate. The migration of the carboxylate group was proved by radioactive labeling. At higher pH‐values (pH > 11,5) the intakt ester group migrates, with ester hydrolysis occuring as a second step.