5‐vinylisoxazole

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Abstract
Cycloaddition of fulminic acid to 1‐butyn‐3‐ol gave a mixture of 5‐α‐hydroxyethylisoxazole (I) and 4‐α‐hydroxyethylisoxazole (II) in the ratio 9:1. By the dehydration of 1, 5‐vinylisoxazole (III) was obtained. Compound III has also been prepared by cyclization of 4‐penten‐2‐ynal as well as its diethylacetal with hydroxylamine hydrochloride; in both instances no isomers have been obtained. Compound III spontaneously polymerizes even at room temperature yielding a polymer still containing isoxazole rings.