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Title: Support for a Dioxyallyl Cation in the Mechanism Leading to (−)-Levoglucosenone
Contributor(s): Greatrex, Ben (author)orcid ; Meisner, Jan (author); Glover, Stephen (author); Raverty, Warwick (author)
Publication Date: 2017
DOI: 10.1021/acs.joc.7b02109
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Abstract: Levoglucosenone (LGO) is the major product formed when cellulose is pyrolyzed in the presence of acid at temperatures between 170 and 350 °C. The current intense interest in biomass conversion has led to a number of reports on its preparation; however, there is still uncertainty on the mechanism leading to LGO. We propose a new mechanism which involves a C2-C1 hydride shift followed by intramolecular trapping of a dioxyallyl cation. The reaction has been modeled using DFT calculations from the known LGO precursors levoglucosan and 1,4:3,6-dianhydro-α-D-glucopyranose to a common intermediate with calculated barriers of 10.6 and 13.5 kcal·mol-1, respectively. A discussion of the literature on the formation of LGO from late pathway intermediates is also provided.
Publication Type: Journal Article
Source of Publication: The Journal of Organic Chemistry, 82(23), p. 12294-12299
Publisher: American Chemical Society
Place of Publication: United States of America
ISSN: 1520-6904
Field of Research (FOR): 030505 Physical Organic Chemistry
030504 Organic Green Chemistry
030503 Organic Chemical Synthesis
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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Appears in Collections:Journal Article
School of Rural Medicine

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