Journal of Organic Chemistry p. 1753 - 1757 (1990)
Update date:2022-08-05
Topics:
Lenz, George R.
Costanza, Carl
Lessor, Ralph A.
Ezell, Edward F.
Oxidation of the acyclic N-(1-(1-naphthyl)vinyl)urethane (3) with lead tetraacetate (LTA) forms a naphthyloxazolone as the major product, accompanied by the product of rearrangement, N-(ethoxycarbonyl)-1-naphthylacetamide.When the naphthyl group is replaced by alkoxy-substituted aromatic rings, the N-vinylurethane undergoes three successive oxidations by LTA leading to novel substituted nitrogen containing cyclic anhydrides, oxazolidine-2,5-diones.The structure of this unusual oxidation product was proven by X-ray analysis.The mechanism of the oxidation is discussed in terms of known enamide oxidations, and the intermediacy of an oxazolone is demonstrated.
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