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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/59165
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dc.contributor.authorPuschnig, Johannesen
dc.contributor.authorGreatrex, Ben Wen
dc.date.accessioned2024-05-10T06:40:41Z-
dc.date.available2024-05-10T06:40:41Z-
dc.date.issued2024-03-01-
dc.identifier.citationEuropean Journal of Organic Chemistry, 27(9), p. 1-5en
dc.identifier.issn1099-0690en
dc.identifier.issn1434-193Xen
dc.identifier.urihttps://hdl.handle.net/1959.11/59165-
dc.description.abstract<p>A ring-expansion process for the biomass derivative Cyrene obtained from levoglucosenone has been developed using gem-dihalocyclopropanes as intermediates. The process involves conversion of Cyrene to an enamine, reaction with an in situ generated dihalocarbene, and then ring-opening. Competition between endocyclic and exocyclic olefinic products was switchable using solvent and temperature, and ringexpanded alkenyl halides were obtained in 50–64% yield from Cyrene. Under extended heating, dehalogenation occurred giving homologated levoglucosenone in 25% overall yield from Cyrene in 3 steps.</p>en
dc.languageenen
dc.publisherWiley-VCH Verlag GmbH & Co. KGaAen
dc.relation.ispartofEuropean Journal of Organic Chemistryen
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.titleRing-Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanationen
dc.typeJournal Articleen
dc.identifier.doi10.1002/ejoc.202400031en
dcterms.accessRightsUNE Greenen
local.contributor.firstnameJohannesen
local.contributor.firstnameBen Wen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.publisher.placeGermanyen
local.identifier.runningnumbere202400031en
local.format.startpage1en
local.format.endpage5en
local.peerreviewedYesen
local.identifier.volume27en
local.identifier.issue9en
local.access.fulltextYesen
local.contributor.lastnamePuschnigen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:1959.11/59165en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleRing-Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanationen
local.relation.fundingsourcenoteJ.P. thanks the Australian Government for a Research Training Program (RTP) Scholarship and a Destination Australia Program Scholarship.en
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorPuschnig, Johannesen
local.search.authorGreatrex, Ben Wen
local.open.fileurlhttps://rune.une.edu.au/web/retrieve/9abb11c9-86b4-4a7c-a18d-55bd48a1c690en
local.uneassociationYesen
local.atsiresearchNoen
local.sensitive.culturalNoen
local.year.published2024en
local.fileurl.openhttps://rune.une.edu.au/web/retrieve/9abb11c9-86b4-4a7c-a18d-55bd48a1c690en
local.fileurl.openpublishedhttps://rune.une.edu.au/web/retrieve/9abb11c9-86b4-4a7c-a18d-55bd48a1c690en
local.subject.for20203405 Organic chemistryen
local.profile.affiliationtypeUNE Affiliationen
local.profile.affiliationtypeUNE Affiliationen
local.date.moved2024-05-10en
Appears in Collections:Journal Article
School of Rural Medicine
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