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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/61672
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dc.contributor.authorJevric, Martynen
dc.contributor.authorKlepp, Julianen
dc.contributor.authorPuschnig, Johannesen
dc.contributor.authorLamb, Oscaren
dc.contributor.authorSumby, Christopher Jen
dc.contributor.authorGreatrex, Ben Wen
dc.date.accessioned2024-07-16T04:19:40Z-
dc.date.available2024-07-16T04:19:40Z-
dc.date.issued2024-04-16-
dc.identifier.citationBeilstein Journal of Organic Chemistry, v.20, p. 823-829en
dc.identifier.issn1860-5397en
dc.identifier.issn2195-951Xen
dc.identifier.urihttps://hdl.handle.net/1959.11/61672-
dc.description.abstract<p>A skeletal rearrangement of a series of 6,8-dioxabicyclo[3.2.1]octan-4-ols has been developed using SOCl<sub>2</sub> in the presence of pyridine. An oxygen migration from C5 to C4 was observed when the C4 alcohols were treated with SOCl<sub>2</sub>/pyridine, giving a 2-chloro3,8-dioxabicyclo[3.2.1]octane ring-system via the chlorosulfite intermediate. Analogous allylic alcohols with endocyclic and exocyclic unsaturations underwent chlorination without rearrangement due to formation of allylic cations. The rearrangement was also demonstrated using Appel conditions, which gave similar results via the alkoxytriphenylphosphonium intermediate. Several reactions of the products were investigated to show the utility of the rearrangement.</p>en
dc.languageenen
dc.publisherBeilstein - Institut zur Foerderung der Chemischen Wissenschaftenen
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleSkeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditionsen
dc.typeJournal Articleen
dc.identifier.doi10.3762/bjoc.20.74en
dc.identifier.pmid38655557en
dcterms.accessRightsUNE Greenen
local.contributor.firstnameMartynen
local.contributor.firstnameJulianen
local.contributor.firstnameJohannesen
local.contributor.firstnameOscaren
local.contributor.firstnameChristopher Jen
local.contributor.firstnameBen Wen
local.profile.schoolSchool of Rural Medicineen
local.profile.schoolSchool of Science and Technologyen
local.profile.schoolSchool of Science and Technologyen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailmjevric@une.edu.auen
local.profile.emailjklepp3@une.edu.auen
local.profile.emailolamb2@une.edu.auen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.publisher.placeGermanyen
local.format.startpage823en
local.format.endpage829en
local.peerreviewedYesen
local.identifier.volume20en
local.access.fulltextYesen
local.contributor.lastnameJevricen
local.contributor.lastnameKleppen
local.contributor.lastnamePuschnigen
local.contributor.lastnameLamben
local.contributor.lastnameSumbyen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:mjevricen
dc.identifier.staffune-id:jklepp3en
dc.identifier.staffune-id:olamb2en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:1959.11/61672en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleSkeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditionsen
local.relation.fundingsourcenoteJP was supported by an Australian Government Research Training Program Scholarship and the Destination Australia Program.en
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorJevric, Martynen
local.search.authorKlepp, Julianen
local.search.authorPuschnig, Johannesen
local.search.authorLamb, Oscaren
local.search.authorSumby, Christopher Jen
local.search.authorGreatrex, Ben Wen
local.open.fileurlhttps://rune.une.edu.au/web/retrieve/7ad92e86-846f-44f5-8c1f-7799995a6ca4en
local.uneassociationYesen
local.atsiresearchNoen
local.sensitive.culturalNoen
local.year.published2024en
local.fileurl.openhttps://rune.une.edu.au/web/retrieve/7ad92e86-846f-44f5-8c1f-7799995a6ca4en
local.fileurl.openpublishedhttps://rune.une.edu.au/web/retrieve/7ad92e86-846f-44f5-8c1f-7799995a6ca4en
local.subject.for20203405 Organic chemistryen
local.profile.affiliationtypeUNE Affiliationen
local.profile.affiliationtypeUNE Affiliationen
local.profile.affiliationtypeUNE Affiliationen
local.profile.affiliationtypeUNE Affiliationen
local.profile.affiliationtypeExternal Affiliationen
local.profile.affiliationtypeUNE Affiliationen
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology
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