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Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans

Yilmaz, Mehmet; Yilmaz, E. Vildan Burgaz; Pekel, A. Tarik


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/20777</identifier>
  <creators>
    <creator>
      <creatorName>Yilmaz, Mehmet</creatorName>
      <givenName>Mehmet</givenName>
      <familyName>Yilmaz</familyName>
      <affiliation>Kocaeli Univ, Dept Chem, Fac Arts &amp; Sci, TR-41380 Umuttepe, Kocaeli, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Yilmaz, E. Vildan Burgaz</creatorName>
      <givenName>E. Vildan Burgaz</givenName>
      <familyName>Yilmaz</familyName>
      <affiliation>Ankara Univ, Fac Sci, Dept Chem, TR-06100 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Pekel, A. Tarik</creatorName>
      <givenName>A. Tarik</givenName>
      <familyName>Pekel</familyName>
      <affiliation>Ankara Univ, Fac Sci, Dept Chem, TR-06100 Ankara, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Radical Cyclization Of Fluorinated 1,3-Dicarbonyl Compounds With Dienes Using Manganese(Iii) Acetate And Synthesis Of Fluoroacylated 4,5-Dihydrofurans</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/20777</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/hlca.201100105</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">Radical cyclizations of fluorinated 1,3-dicarbonyl compounds with dienes mediated by Mn(OAc)3 afforded 4,5-dihydrofurans containing difluoroacetyl, trifluoroacetyl, or heptafluorobutanoyl groups in good-to-excellent yields. Additionally, 2-(difluoromethyl)-4,5-dihydrofurans and a 4,7-dihydrooxepin derivative were obtained as unexpected products in the reaction of 4,4-difluoro-1-phenylbutane-1,3-dione with 1,3-diphenylbuta-1,3-diene. The radical cyclization of symmetrical dienes such as 2,3-dimethylbuta-1,3-diene and 1,4-diphenylbuta-1,3-diene with 1,3-diketones furnished the corresponding products in low yields. However, treatment of 1-phenylbuta-1,3-diene with 1,3-dicarbonyl compounds afforded 4,5-dihydrofurans containing fluoroacyl groups. The radical cyclizations with 3-methyl-1-phenylbuta-1,3-diene and 1,3-diphenylbuta-1,3-diene led to 4,5-dihydrofurans in good yields, since Me and Ph groups at C(3) of these dienes increase the stability of the radical intermediate.</description>
  </descriptions>
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