The Acid-catalyzed Isomerization of an α-Ketoester into β-Ketoesters and the Unusual Fragmentation of an α-Ketoester. Preliminary communication

The first example of an acid‐catalyzed isomerization of an α‐ketoester into β‐ketoesters is described. Ethyl 2‐keto‐3,3‐diphenylbutyrate rearranged in fluorosulfonic acid at 0° into ethyl 2‐benzoyl‐2‐phenylpropionate and ethyl 2,2‐diphenylacetoacetate. In contrast, fragmentation of ethyl 3,3‐dipheny...

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Veröffentlicht in:Helvetica chimica acta 1972-07, Vol.55 (6), p.2255-2257
Hauptverfasser: Kagan, Jacques, Agdeppa Jr, Dalmacio A.
Format: Artikel
Sprache:eng
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Zusammenfassung:The first example of an acid‐catalyzed isomerization of an α‐ketoester into β‐ketoesters is described. Ethyl 2‐keto‐3,3‐diphenylbutyrate rearranged in fluorosulfonic acid at 0° into ethyl 2‐benzoyl‐2‐phenylpropionate and ethyl 2,2‐diphenylacetoacetate. In contrast, fragmentation of ethyl 3,3‐diphenylpyruvate to benzophenone occurred in the same conditions.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19720550649