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Synthesis 1991; 1991(12): 1205-1208
DOI: 10.1055/s-1991-28420
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Synthesis and Reactions of Functionalized Perfluoroalkyl Sulfones

Michael Hanack* , Günter Bailer, Jürgen Hackenberg, L. R. Subramanian
  • *Institut für Organische Chemie, Lehrstuhl für Organische Chemie II der Universität Tübingen, Auf der Morgenstelle 18, D-7400 Tübingen 1, Germany
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Publication Date:
29 April 2002 (online)

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The hitherto unknown 2-aryl-1-(perfluoroalkanesulfonyl)acrylonitriles 9 (RF = CF3, C4F9) were prepared by Knoevenagel condensation of (perfluoroalkanesulfonyl)acetonitriles 7 with aromatic aldehydes. The nitriles 7 were prepared in one-step by reaction of the lithium salt of acetonitrile with nonafluorobutanesulfonyl- and trifluoromethanesulfonyl fluoride, respectively, in modest yield. The reactivity of 9 in Diels-Alder reactions with 2,3-dimethylbutadiene and cyclopentadiene was studied.

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