C. Chuaqui, Sabine Delaney, J. Merritt
1983
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron
Abstract
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. The results strongly suggest that III is formed after O2 has abstracted a proton from II, and then, species resulting from secondary reactions, such as oxygen, attack II to yield the final products. Several mechanistic pathways are discussed.