1 Ocak 2011 Dergi makalesi Açık Erişim

Ucuncu, Muhammed; Karakus, Erman; Kus, Melih; Akpinar, Gurkan Eray; Aksin-Artok, Oezge; Krause, Norbert; Karaca, Sila; Elmaci, Nuran; Artok, Levent

Dublin Core

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  <dc:creator>Ucuncu, Muhammed</dc:creator>
  <dc:creator>Karakus, Erman</dc:creator>
  <dc:creator>Kus, Melih</dc:creator>
  <dc:creator>Akpinar, Gurkan Eray</dc:creator>
  <dc:creator>Aksin-Artok, Oezge</dc:creator>
  <dc:creator>Krause, Norbert</dc:creator>
  <dc:creator>Karaca, Sila</dc:creator>
  <dc:creator>Elmaci, Nuran</dc:creator>
  <dc:creator>Artok, Levent</dc:creator>
  <dc:date>2011-01-01</dc:date>
  <dc:description>Two methods involving the rhodium-catalyzed reaction of 2-en-4-yne acetates and the palladium-catalyzed reaction of 2-en-4-yne carbonates with organoboronic acids were investigated; both afforded exclusively the (E)-configured vinylallenes. The coordinative interaction of the rhodium with the acetate group promoted the delta-elimination of Rh(I)-OAc from the alkenylrhodium intermediate II in both syn and anti modes, with the syn-elimination being the major path. DFT calculations revealed that a conformer of this intermediate (II), which can lead to the (E)-configured vinylallene product via the syn-elimination mode, is energetically the most favorable conformer. The rhodium-catalyzed procedure is not applicable to reactions involving (E)-configured enyne acetates, because the geometry of the alkenylrhodium intermediate that is derived from the corresponding (E)-enyne acetate would not allow such coordinative interaction to occur, The palladium-catalyzed method, which proceeds through formation of the c-vinylallenylpalladium intermediate, B, is suitable for both the (E)- and (Z)-configured enyne carbonates and appears to have a wider scope for both organoboronic acids and enyne substrates. The palladium-catalyzed reaction of an enantiomerically enriched enyne carbonate proceeded with racemization.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/21447</dc:identifier>
  <dc:identifier>oai:zenodo.org:21447</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>JOURNAL OF ORGANIC CHEMISTRY 76(15) 5959-5971</dc:source>
  <dc:title>Rhodium- and Palladium-Catalyzed 1,5-Substitution Reactions of 2-En-4-yne Acetates and Carbonates with Organoboronic Acids</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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