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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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{
  "DOI": "10.1002/hlca.201100105", 
  "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.", 
  "author": [
    {
      "family": "Yilmaz", 
      "given": " Mehmet"
    }, 
    {
      "family": "Yilmaz", 
      "given": " E. Vildan Burgaz"
    }, 
    {
      "family": "Pekel", 
      "given": " A. Tarik"
    }
  ], 
  "container_title": "HELVETICA CHIMICA ACTA", 
  "id": "20777", 
  "issue": "11", 
  "issued": {
    "date-parts": [
      [
        2011, 
        1, 
        1
      ]
    ]
  }, 
  "page": "2027-2038", 
  "title": "Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans", 
  "type": "article-journal", 
  "volume": "94"
}
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