Umlagerung und Spaltung von α, β‐Dioxopropionsäureestern in alkalischem Milieu. 28. Mitt. über Reduktone und Tricarbonylverbindungen [1]

Abstract

The behaviour of α,β‐dioxopropionic acid derivatives of the type RCOCOCOX (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 RCOOH 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.