Tetravinylethylene
| dc.contributor.author | Lindeboom, Erik | en_AU |
| dc.contributor.author | Willis, Anthony | en_AU |
| dc.contributor.author | Paddon-Row, Michael | en_AU |
| dc.contributor.author | Sherburn, Michael | en_AU |
| dc.date.accessioned | 2015-12-10T23:09:11Z | |
| dc.date.issued | 2014 | |
| dc.date.updated | 2015-12-10T09:11:04Z | |
| dc.description.abstract | The first four-fold cross coupling reaction involving alkenic partners leads to the title hydrocarbon on multi-gram scale in one step from commercially available precursors. In stark contrast to its close structural relatives, tetravinylethylene is a remarkably robust, bench-stable compound. The π-bond rich hydrocarbon is shown to undergo one-pot sequences of pericyclic reactions leading to the formation of complex systems with four new rings, seven C-C bonds and ten stereocenters with a very high level of stereoselectivity. Insights into the reactivity of this and related systems is provided using the accurate composite ab initio MO G4(MP2) method. Targets very efficiently: The forgotten hydrocarbon, tetravinylethylene (TVE, scheme) is a bench-stable compound that can be synthesized in one step from commercially available starting materials. TVE is a vehicle for rapid complex molecule synthesis through one-pot sequences involving the stereoselective assembly of up to seven C-C bonds. | |
| dc.identifier.issn | 1433-7851 | |
| dc.identifier.uri | http://hdl.handle.net/1885/63370 | |
| dc.publisher | Wiley-VCH Verlag GMBH | |
| dc.source | Angewandte Chemie International Edition | |
| dc.title | Tetravinylethylene | |
| dc.type | Journal article | |
| local.bibliographicCitation.issue | 21 | |
| local.bibliographicCitation.lastpage | 5443 | |
| local.bibliographicCitation.startpage | 5440 | |
| local.contributor.affiliation | Lindeboom, Erik, College of Physical and Mathematical Sciences, ANU | |
| local.contributor.affiliation | Willis, Anthony, College of Physical and Mathematical Sciences, ANU | |
| local.contributor.affiliation | Paddon-Row, Michael, University of New South Wales | |
| local.contributor.affiliation | Sherburn, Michael, College of Physical and Mathematical Sciences, ANU | |
| local.contributor.authoremail | u4819037@anu.edu.au | |
| local.contributor.authoruid | Lindeboom, Erik, u4819037 | |
| local.contributor.authoruid | Willis, Anthony, u8512028 | |
| local.contributor.authoruid | Sherburn, Michael, u4053118 | |
| local.description.embargo | 2037-12-31 | |
| local.description.notes | Imported from ARIES | |
| local.identifier.absfor | 030503 - Organic Chemical Synthesis | |
| local.identifier.absseo | 970103 - Expanding Knowledge in the Chemical Sciences | |
| local.identifier.ariespublication | u4005981xPUB798 | |
| local.identifier.citationvolume | 53 | |
| local.identifier.doi | 10.1002/anie.201402840 | |
| local.identifier.scopusID | 2-s2.0-84900845142 | |
| local.identifier.thomsonID | 000335809200036 | |
| local.identifier.uidSubmittedBy | u4005981 | |
| local.type.status | Published Version |
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