کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5270861 | 1385426 | 2010 | 4 صفحه PDF | دانلود رایگان |
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.
Jones oxidation of 2-furylethanols leads directly to β-keto-tetrahydrofurans; similar oxidations using magnesium monoperoxyphthalate generate the likely enedione intermediates while IBX oxidises the alcohols to the corresponding aldehydes.
Journal: Tetrahedron Letters - Volume 51, Issue 4, 27 January 2010, Pages 720-723