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

28 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.",

author = "Xinghua Ma and Natasha Anderson and White, \{Lorenzo V.\} and Song Bae and Warwick Raverty and Willis, \{Anthony C.\} and Banwell, \{Martin G.\}",

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doi = "10.1071/CH14574",

language = "English",

volume = "68",

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journal = "Australian Journal of Chemistry",

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TY - JOUR

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

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/84927772379

U2 - 10.1071/CH14574

DO - 10.1071/CH14574

M3 - Article

SN - 0004-9425

VL - 68

SP - 593

EP - 599

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 4

ER -

The conversion of levoglucosenone into isolevoglucosenone

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