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

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/21447</identifier>
  <creators>
    <creator>
      <creatorName>Ucuncu, Muhammed</creatorName>
      <givenName>Muhammed</givenName>
      <familyName>Ucuncu</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Karakus, Erman</creatorName>
      <givenName>Erman</givenName>
      <familyName>Karakus</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kus, Melih</creatorName>
      <givenName>Melih</givenName>
      <familyName>Kus</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Akpinar, Gurkan Eray</creatorName>
      <givenName>Gurkan Eray</givenName>
      <familyName>Akpinar</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Aksin-Artok, Oezge</creatorName>
      <givenName>Oezge</givenName>
      <familyName>Aksin-Artok</familyName>
      <affiliation>Dortmund Univ Technol, D-44227 Dortmund, Germany</affiliation>
    </creator>
    <creator>
      <creatorName>Krause, Norbert</creatorName>
      <givenName>Norbert</givenName>
      <familyName>Krause</familyName>
      <affiliation>Dortmund Univ Technol, D-44227 Dortmund, Germany</affiliation>
    </creator>
    <creator>
      <creatorName>Karaca, Sila</creatorName>
      <givenName>Sila</givenName>
      <familyName>Karaca</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Elmaci, Nuran</creatorName>
      <givenName>Nuran</givenName>
      <familyName>Elmaci</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Artok, Levent</creatorName>
      <givenName>Levent</givenName>
      <familyName>Artok</familyName>
      <affiliation>Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Izmir, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Rhodium- And Palladium-Catalyzed 1,5-Substitution Reactions Of 2-En-4-Yne Acetates And Carbonates With Organoboronic Acids</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2011</publicationYear>
  <dates>
    <date dateType="Issued">2011-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/21447</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/jo200201r</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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.</description>
  </descriptions>
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