Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes
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Saglam, Mehmet F; Fallon, Thomas; Paddon-Row, Michael N; Sherburn, Michael
Description
The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic...[Show more]
dc.contributor.author | Saglam, Mehmet F | |
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dc.contributor.author | Fallon, Thomas | |
dc.contributor.author | Paddon-Row, Michael N | |
dc.contributor.author | Sherburn, Michael | |
dc.date.accessioned | 2018-11-16T06:14:37Z | |
dc.date.available | 2018-11-16T06:14:37Z | |
dc.identifier.issn | 0002-7863 | |
dc.identifier.uri | http://hdl.handle.net/1885/149537 | |
dc.description.abstract | The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences. | |
dc.format.mimetype | application/pdf | |
dc.rights | Author'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 General Conditions: On author's personal website, pre-print servers, institutional website, institutional repositories or subject repositories Non-Commercial Must be accompanied by set statement (see policy) Must link to publisher version Publisher's version/PDF cannot be used | |
dc.source | Journal of the American Chemical Society | |
dc.subject | alkenes | |
dc.subject | cycloaddition reaction | |
dc.subject | molecular conformation | |
dc.title | Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes | |
dc.type | Journal article | |
local.identifier.citationvolume | 138 | |
dc.date.issued | 2016-01-27 | |
local.type.status | Metadata only | |
local.contributor.affiliation | Research School of Chemistry | |
local.identifier.essn | 1520-5126 | |
local.bibliographicCitation.issue | 3 | |
local.bibliographicCitation.startpage | 1022-32 | |
local.bibliographicCitation.lastpage | 1032 | |
local.identifier.doi | 10.1021/jacs.5b11889 | |
dcterms.accessRights | Open Access | |
Collections | ANU Research Publications |
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