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Umlagerung und Spaltung von α, β‐Dioxopropionsäureestern in alkalischem Milieu. 28. Mitt. über Reduktone und Tricarbonylverbindungen [1]
Author(s) -
RodéGowal Heike,
Dao Huu Lé,
Dahn Hans
Publication year - 1974
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.19740570737
Subject(s) - chemistry , glyoxylic acid , medicinal chemistry , steric effects , hydrolysis , stereochemistry , organic chemistry
The behaviour of α,β‐dioxopropionic acid derivatives of the type RCOCOCOX (R = phenyl, p ‐substituted phenyls, CF 3 , mesityl; X = OC 2 H 5 , NH 2 ) was investigated under benzilic acid rearrangement conditions. Nearly all compounds were cleaved by alkali to give the corresponding acids RCOOH and glyoxylic acid. Only the sterically hindered ethyl β‐mesityl‐α,β‐dioxopropionate underwent rearrangement (after hydrolysis of the ester group); it was shown by 14 C‐labelling that the carboxylate group migrates to the β‐carbonyl group.