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RESEARCH ARTICLE
Contents Vol 68(4)

The Conversion of Levoglucosenone into Isolevoglucosenone*

Xinghua Ma A , Natasha Anderson A , Lorenzo V. White A , Song Bae A , Warwick Raverty B , Anthony C. Willis A and Martin G. Banwell A C
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 2601, Australia.

B Circa Group Pty Ltd, 34 Norfolk Court, Coburg North Vic. 3058, Australia.

C Corresponding author. Email: Martin.Banwell@anu.edu.au

Australian Journal of Chemistry 68(4) 593-599 https://doi.org/10.1071/CH14574
Submitted: 18 September 2014  Accepted: 15 October 2014   Published: 27 January 2015

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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