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

Article abstract of DOI:10.1016/S0040-4020(01)92156-8

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.