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Synthesis of 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone |
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| Authors: | Dmitri V Sevenard Olesya Kazakova Gerd-Volker Röschenthaler |
| Institution: | a Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Str., 28334 Bremen, Germany b Hansa Fine Chemicals GmbH, Leobener Str., 28334 Bremen, Germany c Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch, S. Kovalevskoy Str. 22, 620219 Ekaterinburg, Russia |
| Abstract: | A simple, convenient and effective method to synthesize 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone, on a preparative scale was developed. The title compound was obtained by a Claisen-type double condensation of acetone with trifluoroacetic acid ethyl ester and isolated as a solid monohydrate from the reaction mixture. Subsequent dehydration proceeds smoothly to produce the desired compound as an individual substance. Its peculiar tautomeric (keto-enol, ring-chain) features in various solvents are discussed. |
| Keywords: | Building blocks Fluorinated 1 3 5-triketones Preparative synthesis Ring-chain tautomerism Pyran Enol |
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