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- W1999295990 abstract "Bei der Acylierung von Δ2-Oxazolinonen-(5) mit Carbonsäureanhydriden/Pyridin entstehen neben 4-Acyl-Δ2-oxazolinonen 2 auch 5-Acyloxy-oxazole 4, [N-Acyl-dihydropyridyl]-Δ2-oxazolinone 5 und 2-Acyl-Δ3-oxazolinone 7, die sich mehr oder weniger leicht in das thermodynamisch stabilste Acylderivat 2 umwandeln. Als gemeinsame Zwischenstufe wird ein Ionenpaar 6 angenommen, das die spezifische katalytische Wirksamkeit von Pyridinbasen bei der Dakin-West-Reaktion zwanglos erklärt. Ist die Umlagerung von 7 in 2 aus sterischen Gründen erschwert, so können unter Dakin-West-Bedingungen durch Cycloeliminierung von CO2 Oxazole 8 entstehen. Weitere „Störreaktionen”︁ wie Acylaustausch und die Bildung eines Imidazolderivates 13 werden diskutiert. Contributions to the Mechanism of the Dakin-West Reaction, II. Acylation of Δ2-Oxazolin-5-ones by Carboxylic Anhydrides/Pyridine The acylation of Δ2-oxazolin-5-ones by carboxylic anhydrides/pyridine affords, besides 4-acyl-Δ2-oxazolinones 2, also 5-acyloxy-oxazoles 4, [N-acyl-dihydropyridyl]-Δ2-oxazolinones 5 and 2-acyl-Δ3-oxazolinones 7, which are then converted into the thermodynamically most stable acyl derivative 2 more or less easily. As a common intermediate the ion pair 6 is postulated, which explains the specific catalytic efficiency of pyridine bases in the Dakin-West reaction. In case of steric hindrance in the rearrangement 7 → 2, 7 may yield oxazoles 8 via cycloelimination of CO2. Further side reactions like acyl exchange and formation of an imidazole derivative 13 are discussed." @default.
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- W1999295990 title "Zum Mechanismus der Dakin‐West‐Reaktion, II. Acylierung von Δ <sup>2</sup> ‐Oxazolinonen‐(5) mit Carbonsäureanhydriden/Pyridin" @default.
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- W1999295990 doi "https://doi.org/10.1002/cber.19711041130" @default.
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