Über die Wanderung der Carboxylatgruppe bei der Benzilsäureumlagerung. 26. Mitteilung über Reduktone und Tricarbonylverbindungen | Zendy

RodéGowal Heike | Zendy; Dahn Hans | Zendy

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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.

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