Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene
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Liu, Xin
Pollard, Brett
Banwell, Martin
Yu, Li-Juan
Coote, Michelle
Gardiner, Michael
van Vugt-Lussenburg, Barbara M. A.
van der Burg, Bart
Grasset, Fabien L.
Campillo, Elisabeth
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CSIRO Publishing
Abstract
The bio-derived platform molecule levoglucosenone (LGO, 1), which is the precursor to the green solvent Cyrene (2), has been converted, at multi-gram scale, into itspseudo-enantiomer (iso-LGO, 2) and this reduced to iso-Cyrene (4). A less effective synthesis of this last compound from D-glucose is also described. Various physicochemical as well as certain toxicological properties of compound 4 are reported and compared to those established for the now commercially available Cyrene (2). Such studies reveal that there are significant enough differences in the properties of the sustainably-derived Cyrene (2) and isomer 4 (iso-Cyrene) to suggest they will exert complementary effects as solvents in a range of
settings.
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Australian Journal of Chemistry
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Author Accepted Manuscript