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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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  <dc:creator>Yilmaz, Mehmet</dc:creator>
  <dc:creator>Yilmaz, E. Vildan Burgaz</dc:creator>
  <dc:creator>Pekel, A. Tarik</dc:creator>
  <dc:date>2011-01-01</dc:date>
  <dc:description>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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/20777</dc:identifier>
  <dc:identifier>oai:zenodo.org:20777</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>HELVETICA CHIMICA ACTA 94(11) 2027-2038</dc:source>
  <dc:title>Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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