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The conversion of levoglucosenone into isolevoglucosenone

Ma, Xinghua; Anderson, Natasha; White, Lorenzo; Bae, Song; Raverty, Warwick; Willis, Anthony; Banwell, Martin


Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the...[Show more]

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH14574


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