The conversion of levoglucosenone into isolevoglucosenone

Xinghua Ma; Natasha Anderson; Lorenzo V. White; Song Bae; Warwick Raverty; Anthony C. Willis; Martin G. Banwell

doi:10.1071/CH14574

The conversion of levoglucosenone into isolevoglucosenone

Xinghua Ma, Natasha Anderson, Lorenzo V. White, Song Bae, Warwick Raverty, Anthony C. Willis, Martin G. Banwell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

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 resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

Original language	English
Pages (from-to)	593-599
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	68
Issue number	4
DOIs	https://doi.org/10.1071/CH14574
Publication status	Published - 2015

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title = "The conversion of levoglucosenone into isolevoglucosenone",

abstract = "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 resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.",

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T1 - The conversion of levoglucosenone into isolevoglucosenone

AU - Ma, Xinghua

AU - Anderson, Natasha

AU - White, Lorenzo V.

AU - Bae, Song

AU - Raverty, Warwick

AU - Willis, Anthony C.

AU - Banwell, Martin G.

PY - 2015

Y1 - 2015

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AB - 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 resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

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JO - Australian Journal of Chemistry

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The conversion of levoglucosenone into isolevoglucosenone

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