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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
23
pubmed:dateCreated
2010-11-10
pubmed:abstractText
4-(2-Phenylethynyl)-2H-chromen-2-one reacts with norbornene and Co(2)(CO)(8) in an intermolecular Pauson-Khand reaction by focused microwave dielectric heating. Two regioisomeric products are formed; the electron-deficient coumarin moiety preferentially occupies the ?-position of the cyclopentenone ring system, whereas the phenyl occupies the ?-position. The sterically hindered ?,?-(2,3)-disubstituted cyclopentenone regioisomeric products exhibit pronounced atropisomerisation, and the magnitude of the energetic barrier to interconversion between these atropisomers is dependent on the relative position of the coumarin moieties. Interconversion is slow when the coumarin is found in the ?-position, whereas interconversion is relatively fast when found in the ?-position.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Dec
pubmed:issn
1477-0539
pubmed:author
pubmed:issnType
Electronic
pubmed:day
7
pubmed:volume
8
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
5398-403
pubmed:year
2010
pubmed:articleTitle
Atropisomerisation in sterically hindered ?,?-disubstituted cyclopentenones derived from an intermolecular cobalt(0)-mediated Pauson-Khand reaction.
pubmed:affiliation
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
pubmed:publicationType
Journal Article