Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/22784
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dc.contributor.authorGreatrex, Benen
dc.contributor.authorMeisner, Janen
dc.contributor.authorGlover, Stephenen
dc.contributor.authorRaverty, Warwicken
dc.date.accessioned2018-04-12T15:36:00Z
dc.date.issued2017en
dc.identifier.citationThe Journal of Organic Chemistry, 82(23), p. 12294-12299en
dc.identifier.issn1520-6904en
dc.identifier.issn0022-3263en
dc.identifier.urihttps://hdl.handle.net/1959.11/22784en
dc.description.abstractLevoglucosenone (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.en
dc.languageenen
dc.publisherAmerican Chemical Societyen
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.titleSupport for a Dioxyallyl Cation in the Mechanism Leading to (−)-Levoglucosenoneen
dc.typeJournal Articleen
dc.identifier.doi10.1021/acs.joc.7b02109en
dc.subject.keywordsOrganic Green Chemistryen
dc.subject.keywordsOrganic Chemical Synthesisen
dc.subject.keywordsPhysical Organic Chemistryen
local.contributor.firstnameBenen
local.contributor.firstnameJanen
local.contributor.firstnameStephenen
local.contributor.firstnameWarwicken
local.subject.for2008030505 Physical Organic Chemistryen
local.subject.for2008030504 Organic Green Chemistryen
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Rural Medicineen
local.profile.schoolSchool of Science and Technologyen
local.profile.emailbgreatre@une.edu.auen
local.profile.emailsglover@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20180119-13401en
local.publisher.placeUnited States of Americaen
local.format.startpage12294en
local.format.endpage12299en
local.peerreviewedYesen
local.identifier.volume82en
local.identifier.issue23en
local.contributor.lastnameGreatrexen
local.contributor.lastnameMeisneren
local.contributor.lastnameGloveren
local.contributor.lastnameRavertyen
dc.identifier.staffune-id:bgreatreen
dc.identifier.staffune-id:sgloveren
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:22968en
local.identifier.handlehttps://hdl.handle.net/1959.11/22784en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleSupport for a Dioxyallyl Cation in the Mechanism Leading to (−)-Levoglucosenoneen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.description.statisticsepubsVisitors: 7<br />Views: 83<br />Downloads: 0en
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology
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