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

✍ Scribed by Heike Rodé-Gowal; Huu Lé Dao; Hans Dahn

• Publisher: John Wiley and Sons
• Year: 1974
• Tongue: German
• Weight: 463 KB
• Volume: 57
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19740570737

✦ Synopsis

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.