Tetrahedron

Reactions of 2-phenyl-4, 4-dimethyl-2-oxazolin-5-one and 2-phenyl-4-ethyl-2-oxazolin-5-one with KO2 in aprotic solvents (Issued as AECL No. 7964)

CA Chuaqui, S Delaney, J Merritt

Index: Chuaqui, Claudio A.; Delaney, Sabine; Merritt, John Tetrahedron, 1983 , vol. 39, # 18 p. 2947 - 2951

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Citation Number: 5

Abstract

The reactions of 2-phenyl-4, 4-dimethyl-2-oxazolin-5-one (I) and 2-phenyl-4-ethyl-2-oxazolin- 5-one (II) with KO2 in tetrahydrofuran and freon are studied. Superoxide reacts with I to yield the N-benzoyl-α-aminoacid ring-opening product, indicating that O2 produces a nucleophilic attack at the carbonyl group of the oxazolinone. The oxazolinone II yields, in addition to the N-benzoyl-α-amino derivative, N-propanoyl benzamide (III) as the main reaction product. ...

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