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Nucleophilic 1,2-Shifts of Carboxamide Groups in the Benzil-Benzilic Acid Type Rearrangement of 4-Aryl-2,3-dioxobutyramides and of Quinisatine

✍ Scribed by Heike Gowal; Anita Spiess; Marc Ballenegger; Laurent Due; Hans Moll; Hans-Peter Schlunke; Hans Dahn

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
535 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

1 2, Reductones and Tricarbonyl Compounds, Part 32. Part 31 : [I]. The intermediate products, formulated [lo] as imino-enediols -C(OH)=C(OH)-C(=NH)-, very probably exist in their tautomeric forms -CO-C(OH)=C(NH,)-.

We use hcrc the earlier published formula 5 for convenience.

📜 SIMILAR VOLUMES

Nucleophilic 1,2-Shifts of Alkoxycarbony
Nucleophilic 1,2-Shifts of Alkoxycarbonyl and Carboxylate Groups in the Benzilic-Acid Type Rearrangement of α,β-Dioxobutyric Esters
✍ Heike Gowal; Lê H. Dao; Hans Dahn 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 440 KB

## Abstract __tert__‐Butyl α,β‐dioxobutyrate (hydrate; **1d**) undergoes, at medium or high pH, the benzilic‐acid rearrangement with exclusive 1,2‐shift of the COO(__t__‐Bu) group; the same is true for the corresponding isopropyl ester **1c** and ethyl ester **1b** at high pH, whereas at lower pH,