Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/20947
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dc.contributor.authorGlover, Stephenen
dc.date.accessioned2017-05-18T14:47:00Z-
dc.date.issued2017-
dc.identifier.citationAustralian Journal of Chemistry, 70(4), p. 344-361en
dc.identifier.issn1445-0038en
dc.identifier.issn0004-9425en
dc.identifier.urihttps://hdl.handle.net/1959.11/20947-
dc.description.abstractThis account describes the discovery and development of the HERON reaction, a reaction with special connection to the Heron Island Conferences on Reactive Intermediates and Unusual Molecules. This modern 'named' reaction describes an unusual rearrangement of bisheteroatom-substituted amides RCON(X)(Y) whereby the more electron deficient group, X, migrates from nitrogen to the carbonyl carbon giving an acyl derivative, RC(O)X, and Y-stabilised nitrenes. In it, the origins, mechanistic elucidation, and theoretical validation are described in more or less chronological order. Along that time line we introduce the concepts of 'anomeric amides', 'amidicity' in anomeric amides, and their role in the HERON reaction. All known versions of the reaction that have since been discovered are outlined and a basic understanding of the relative roles of reduced resonance and the anomeric driving force, both functions of the heteroatom substituents at the amide nitrogen, are quantified.en
dc.languageenen
dc.publisherCSIRO Publishingen
dc.relation.ispartofAustralian Journal of Chemistryen
dc.titleDevelopment of the HERON Reaction: A Historical Accounten
dc.typeJournal Articleen
dc.identifier.doi10.1071/ch16683en
dc.subject.keywordsTheoretical and Computational Chemistryen
dc.subject.keywordsOrganic Chemical Synthesisen
dc.subject.keywordsPhysical Organic Chemistryen
local.contributor.firstnameStephenen
local.subject.for2008030505 Physical Organic Chemistryen
local.subject.for2008030799 Theoretical and Computational Chemistry not elsewhere classifieden
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Science and Technologyen
local.profile.emailsglover@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20170304-130154en
local.publisher.placeAustraliaen
local.format.startpage344en
local.format.endpage361en
local.identifier.scopusid85016774387en
local.peerreviewedYesen
local.identifier.volume70en
local.identifier.issue4en
local.title.subtitleA Historical Accounten
local.contributor.lastnameGloveren
dc.identifier.staffune-id:sgloveren
local.profile.orcid0000-0002-9344-8669en
local.profile.roleauthoren
local.identifier.unepublicationidune:21140en
dc.identifier.academiclevelAcademicen
local.title.maintitleDevelopment of the HERON Reactionen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorGlover, Stephenen
local.uneassociationUnknownen
local.year.published2017en
local.fileurl.closedpublishedhttps://rune.une.edu.au/web/retrieve/6251da4f-b6a7-44f4-8248-34c6255b1829en
local.subject.for2020340505 Physical organic chemistryen
local.subject.for2020340503 Organic chemical synthesisen
local.subject.for2020340799 Theoretical and computational chemistry not elsewhere classifieden
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
dc.notification.token5a4e01cb-6254-46e0-9c3c-fb4dd1924253en
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