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Tetravinylallene

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dc.contributor.authorElgindy, Cecile
dc.contributor.authorWard, James
dc.contributor.authorSherburn, Michael
dc.date.accessioned2020-07-08T01:05:12Z
dc.date.issued2019-08-30
dc.date.updated2020-06-23T00:56:20Z
dc.description.abstractThe first chemical synthesis of tetravinylallene (3,5-divinylhepta-1,3,4,6-tetraene) is reported. The final, key step of the synthesis involves a palladium-catalyzed, Negishi-type cross-coupling involving 1,5-transposition of a penta-2-en-4- yn-1-ol methanesulfonate. The unprecedented fundamental hydrocarbon is sufficiently stable to be purified by flash chromatography. A similar synthetic pathway grants access to the first substituted tetravinylallenes, which provide insights into the influence of substitution upon stability and reactivity. Tetravinylallenes are shown to break new ground in swift structural complexity creation, with three novel sequences reported.en_AU
dc.description.sponsorshipThis work was supported by the Australian Research Council (DP160104322). We thank Dr. Hideki Onagi and Chris Blake (Australian National University) for assistance with HPLC separations and NMR experiments, respectively.en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn1433-7851en_AU
dc.identifier.urihttp://hdl.handle.net/1885/205916
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/1320..."Author accepted manuscript can be made open access on non-commercial institutional repository after 12 month embargo" from SHERPA/RoMEO site (as at 15.7.2021).
dc.publisherWiley-VCH Verlag GMBHen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP160104322en_AU
dc.rights© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheimen_AU
dc.sourceAngewandte Chemie International Editionen_AU
dc.titleTetravinylalleneen_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Access
dcterms.dateAccepted2019-08-16
local.bibliographicCitation.issue41en_AU
local.bibliographicCitation.lastpage14577en_AU
local.bibliographicCitation.startpage14573en_AU
local.contributor.affiliationElgindy, Cecile, College of Science, ANUen_AU
local.contributor.affiliationWard, James, College of Science, ANUen_AU
local.contributor.affiliationSherburn, Michael, College of Science, ANUen_AU
local.contributor.authoruidElgindy, Cecile, u5482258en_AU
local.contributor.authoruidWard, James, u4431856en_AU
local.contributor.authoruidSherburn, Michael, u4053118en_AU
local.description.notesImported from ARIESen_AU
local.identifier.absfor030503 - Organic Chemical Synthesisen_AU
local.identifier.absseo970104 - Expanding Knowledge in the Earth Sciencesen_AU
local.identifier.ariespublicationu5786633xPUB1051en_AU
local.identifier.citationvolume58en_AU
local.identifier.doi10.1002/anie.201908496en_AU
local.identifier.scopusID2-s2.0-85072041957
local.type.statusAccepted Versionen_AU

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