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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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  "@context": "https://schema.org/", 
  "@id": 20777, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Kocaeli Univ, Dept Chem, Fac Arts & Sci, TR-41380 Umuttepe, Kocaeli, Turkey", 
      "name": "Yilmaz, Mehmet"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ankara Univ, Fac Sci, Dept Chem, TR-06100 Ankara, Turkey", 
      "name": "Yilmaz, E. Vildan Burgaz"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ankara Univ, Fac Sci, Dept Chem, TR-06100 Ankara, Turkey", 
      "name": "Pekel, A. Tarik"
    }
  ], 
  "datePublished": "2011-01-01", 
  "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.", 
  "headline": "Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans", 
  "identifier": 20777, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans", 
  "url": "https://aperta.ulakbim.gov.tr/record/20777"
}
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Yilmaz, M., Yilmaz, E. V. B. ve Pekel, A. T. (2011). Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans. HELVETICA CHIMICA ACTA, 94(11), 2027–2038. doi:10.1002/hlca.201100105

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