On the curious oxidations of 2-furylethanols |
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Authors: | Simon J Hayes Andrew WT Smith |
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Institution: | a School of Chemistry, Cardiff University, Main College, Park Place, Cardiff CF10 3AT, UK b Technical and Business Development, GlaxoSmithKline, Shewalton Road, Irvine KA11 5AP, UK |
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Abstract: | Rather than giving the corresponding aldehyde or carboxylic acid, Jones oxidation of 5-substituted-2-furylethanols gives rise to high yields of the corresponding dihydro-2-(2-oxoethyl)furan-3(2H)-ones, following Achmatowicz-type oxidative ring opening and subsequent reclosure by a 5-exo Michael addition of the pendant hydroxy group to the enedione function. Other oxidation methods such as a Swern reaction give lower yields of the same products while magnesium perphthalate tends to yield the intermediate enediones, and IBX tends to yield the furyl aldehydes. |
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Keywords: | Oxidation 2-Furyl ethanols Jones Furans Ring opening |
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