Skip navigation
Skip navigation

Practical Synthesis and Reactivity of [3]Dendralene

Bradford, Tanya; Payne, Alan; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael

Description

(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...[Show more]

dc.contributor.authorBradford, Tanya
dc.contributor.authorPayne, Alan
dc.contributor.authorWillis, Anthony
dc.contributor.authorPaddon-Row, Michael
dc.contributor.authorSherburn, Michael
dc.date.accessioned2015-12-07T22:27:20Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/21851
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.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.description.notesImported from ARIES
local.identifier.citationvolume75
dc.date.issued2010
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu2544221xPUB19
local.type.statusPublished Version
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.description.embargo2037-12-31
local.bibliographicCitation.issue2
local.bibliographicCitation.startpage491
local.bibliographicCitation.lastpage494
local.identifier.doi10.1021/jo9024557
dc.date.updated2016-02-24T09:51:24Z
local.identifier.scopusID2-s2.0-75349102024
local.identifier.thomsonID000273400300030
CollectionsANU Research Publications

Download

File Description SizeFormat Image
01_Bradford_Practical_Synthesis_and_2010.pdf1.21 MBAdobe PDF    Request a copy


Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  19 May 2020/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator