Practical Synthesis and Reactivity of [3]Dendralene

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dc.contributor.authorBradford, Tanyaen_AU
dc.contributor.authorPayne, Alanen_AU
dc.contributor.authorWillis, Anthonyen_AU
dc.contributor.authorPaddon-Row, Michaelen_AU
dc.contributor.authorSherburn, Michaelen_AU
dc.date.accessioned2015-12-07T22:27:20Z
dc.date.issued2010
dc.date.updated2016-02-24T09:51:24Z
dc.description.abstract(Chemical Equation Presented) Aconvenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diels-Alder reactivity of [3]dendralene - including double cycloaddition sequences and catalytic enantioselective variant - are reported.
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/21851
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.subjectKeywords: Chemical equations; Diels-Alder; Enantioselective; Protecting group; Solvent free; Specialized equipment; Three-step synthesis; Volatile hydrocarbons; Chromatographic analysis; Hydrocarbons; Chemical reactions; [3]dendralene; alkene derivative; hydrocarbo
dc.titlePractical Synthesis and Reactivity of [3]Dendralene
dc.typeJournal article
local.bibliographicCitation.issue2
local.bibliographicCitation.lastpage494
local.bibliographicCitation.startpage491
local.contributor.affiliationBradford, Tanya, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPayne, Alan, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPaddon-Row, Michael, University of New South Wales
local.contributor.affiliationSherburn, Michael, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu8512028@anu.edu.au
local.contributor.authoruidBradford, Tanya, u4201378
local.contributor.authoruidPayne, Alan, u4055859
local.contributor.authoruidWillis, Anthony, u8512028
local.contributor.authoruidSherburn, Michael, u4053118
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu2544221xPUB19
local.identifier.citationvolume75
local.identifier.doi10.1021/jo9024557
local.identifier.scopusID2-s2.0-75349102024
local.identifier.thomsonID000273400300030
local.identifier.uidSubmittedByu2544221
local.type.statusPublished Version

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