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- W1978762968 abstract "A reaction of 2-(2-nitrobenzoylmethyl)-1,3-dioxolane (3) with hydroxylamine, followed by acid catalyzed cyclization, produced 5-(2-nitrophenyl)isoxazole (5) as the only isolable product, whereas 2-(benzoylmethyl)-1,3-dioxolane (9) under identical conditions produced a 2.5:1 mixture of 3-phenyl and 5-phenylisoxazoles (10 and 11). These findings contradict the literature report that β-keto ethyleneacetals on treatment wiht hydroxylamine produce exclusively 3-substituted isoxazoles. As an additional proof, 3-(2-nitrophenyl)isoxazole (8) was prepared by an unambiguous method via the nitrile oxide route for comparison. The intermediate obtained on treatment of 2-(2-nitrobenzoyl- methyl)-1,3-dioxolane (3) with hydroxylamine was found to be an isomeric mixture of 5-hydroxy-5-(2-nitrophenyl)-2-isoxazoline (4) and the syn and anti mono-oximes (19) (at least in solution), either of which could give 5-(2-nitrophenyl)isoxazole (5) on acid treatment. A mechanistic rationale is provided to explain the anomalous results" @default.
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- W1978762968 date "2010-08-19" @default.
- W1978762968 modified "2023-09-26" @default.
- W1978762968 title "ChemInform Abstract: Reaction of β-Keto Ethyleneacetals with Hydroxylamine: A Correction." @default.
- W1978762968 cites W2950738224 @default.
- W1978762968 doi "https://doi.org/10.1002/chin.199424143" @default.
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