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 |
Official URL: http://dx.doi.org/10.1016/j.tetlet.2009.11.119
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 the furyl aldehydes.
Item Type: | Article |
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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 |
URI: | https://orca.cardiff.ac.uk/id/eprint/22697 |
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