Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/11592
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dc.contributor.authorMo, Guoningen
dc.contributor.authorGlover, Stephenen
dc.date.accessioned2012-10-30T17:45:00Z-
dc.date.issued2002-
dc.identifier.citationJournal of the Royal Chemical Society: Perkin Transactions 2 (10), p. 1728-1739en
dc.identifier.issn1364-5471en
dc.identifier.issn1472-779Xen
dc.identifier.urihttps://hdl.handle.net/1959.11/11592-
dc.description.abstractTreatment of N-acetoxy-N-alkoxyamides or N-alkoxy-N-chloroamides with sodium azide in aqueous acetonitrile results in Sɴ2 displacement of chloride and the formation of reactive N-alkoxy-N-azidoamides. The reaction with N-acetoxy-N-benzyloxybenzamide has been studied kinetically (k294 = 2 L mol⁻¹ s⁻¹) and azidation of N-formyloxy-N-methoxyformamide has been modeled computationally at the pBP/DN*//HF/6-31G* level of theory. The anomeric amides N-alkoxy-N-azidoamides decompose intramolecularly and spontaneously to esters and two equivalents of nitrogen. This extremely exothermic process facilitates the formation, in excellent yields, of highly hindered esters.en
dc.languageenen
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofJournal of the Royal Chemical Society: Perkin Transactions 2en
dc.titleHindered ester formation by Sɴ2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides - novel application of HERON rearrangementsen
dc.typeJournal Articleen
dc.identifier.doi10.1039/B111250Nen
dc.subject.keywordsPhysical Organic Chemistryen
local.contributor.firstnameGuoningen
local.contributor.firstnameStephenen
local.subject.for2008030505 Physical Organic Chemistryen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Science and Technologyen
local.profile.schoolSchool of Science and Technologyen
local.profile.emailgmo2@une.edu.auen
local.profile.emailsglover@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordpes:93en
local.publisher.placeUnited Kingdomen
local.format.startpage1728en
local.format.endpage1739en
local.identifier.scopusid0036026293en
local.peerreviewedYesen
local.identifier.issue10en
local.contributor.lastnameMoen
local.contributor.lastnameGloveren
dc.identifier.staffune-id:gmoen
dc.identifier.staffune-id:sgloveren
local.profile.orcid0000-0002-9344-8669en
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:11791en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleHindered ester formation by Sɴ2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides - novel application of HERON rearrangementsen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorMo, Guoningen
local.search.authorGlover, Stephenen
local.uneassociationUnknownen
local.identifier.wosid000178314300015en
local.year.published2002en
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