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On the curious oxidations of 2-furylethanols

Hayes, Simon, Knight, David William, Smith, Andrew W.T. and O'Halloran, Mark J. 2010. On the curious oxidations of 2-furylethanols. Tetrahedron Letters 51 (4) , pp. 720-723. 10.1016/j.tetlet.2009.11.119

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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 the furyl aldehydes.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Last Modified: 06 May 2023 01:28

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