Skip navigation
Skip navigation

[5]Radialene

Mackay, Emily G; Newton, Christopher G; Toombs-Ruane, Henry; Lindeboom, Erik; Fallon, Thomas; Willis, Anthony C; Paddon-Row, Michael N; Sherburn, Michael

Description

The [n]radialenes are a unique family of fundamental [n]-membered carbocyclic structures with radiating alkenes, which have attracted significant synthetic and theoretical attention. Whereas [3]-, [4]-, and [6]radialenes have been prepared and studied, all efforts to synthesize the five-membered ring compound have thus far met with failure. Here we describe the first synthesis of the fundamental hydrocarbon [5]radialene, C10H10. Our approach was a departure from previous radialene syntheses in...[Show more]

dc.contributor.authorMackay, Emily G
dc.contributor.authorNewton, Christopher G
dc.contributor.authorToombs-Ruane, Henry
dc.contributor.authorLindeboom, Erik
dc.contributor.authorFallon, Thomas
dc.contributor.authorWillis, Anthony C
dc.contributor.authorPaddon-Row, Michael N
dc.contributor.authorSherburn, Michael
dc.date.accessioned2018-11-16T06:07:12Z
dc.date.available2018-11-16T06:07:12Z
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/1885/149535
dc.description.abstractThe [n]radialenes are a unique family of fundamental [n]-membered carbocyclic structures with radiating alkenes, which have attracted significant synthetic and theoretical attention. Whereas [3]-, [4]-, and [6]radialenes have been prepared and studied, all efforts to synthesize the five-membered ring compound have thus far met with failure. Here we describe the first synthesis of the fundamental hydrocarbon [5]radialene, C10H10. Our approach was a departure from previous radialene syntheses in that it utilized a low-temperature decomplexation of a stable organometallic compound, rather than high-temperature elimination or rearrangement. Our strategy was guided by analysis of previous radialene syntheses, which indicated rapid decomposition in oxygen, and ab initio calculations, which revealed an extraordinary susceptibility of [5]radialene to undergo Diels-Alder dimerization/polymerization. The origin of this susceptibility was traced to a small distortion energy associated with the formation of the transition structure geometry from the relaxed reactant monomers and to a narrow HOMO-LUMO gap.
dc.format.mimetypeapplication/pdf
dc.publisherAmerican Chemical Society
dc.rightsAuthor's Pre-print: grey tick subject to Restrictions below, author can archive pre-print (ie pre-refereeing) Restrictions: Must obtain written permission from Editor Must not violate ACS ethical Guidelines Author's Post-print: grey tick subject to Restrictions below, author can archive post-print (ie final draft post-refereeing) Restrictions: If mandated by funding agency or employer/ institution If mandated to deposit before 12 months, must obtain waiver from Institution/Funding agency or use AuthorChoice 12 months embargo Publisher's Version/PDF: cross author cannot archive publisher's version/PDF
dc.sourceJournal of the American Chemical Society
dc.title[5]Radialene
dc.typeJournal article
local.identifier.citationvolume137
dc.date.issued2015-11-25
local.type.statusMetadata only
local.contributor.affiliationResearch School of Chemistry, Australian National University, Canberra, Australian Capital Territory 2601, Australia
local.identifier.essn1520-5126
local.bibliographicCitation.issue46
local.bibliographicCitation.startpage14653-9
local.bibliographicCitation.lastpage14659
local.identifier.doi10.1021/jacs.5b07445
dcterms.accessRightsOpen Access
CollectionsANU Research Publications

Download

There are no files associated with this item.


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