Halogenation of Fluorinated 1,3,5‐Triketones |
| |
| Authors: | Dmitri?V Sevenard Olesya Kazakova Dmitri?L Chizhov Danil?S Yachevskii Enno Lork Jörn Poveleit Valery?N Charushin Gerd‐Volker Röschenthaler |
| |
| Institution: | 1. Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Str., D‐28334 Bremen, (phone: +?49‐421‐218‐3435;2. fax: +?49‐421‐218‐4267);3. Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch, S.?Kovalevskoy Str.?22, 620219 Ekaterinburg, Russia |
| |
| Abstract: | The behavior of linear and cyclic fluorinated 1,3,5‐triketones and their metal derivatives towards common halogenating agents was examined, and optimal reaction conditions for the straightforward synthesis of mono‐, di‐, and tetrahalogenated products were found (Schemes 1–3). An aromatization through a double HBr elimination from an α,α′‐dibrominated cyclohexanone was shown to be a promising synthetic route to 1,1′‐(2‐hydroxy‐1,3‐phenylene)bis2,2,2‐trifluoroethanones] (= 2,6‐bis(trifluoroacetyl)phenols; Scheme 4). Additionally, the 1,3,5‐triketones prepared add readily H2O or alcohols to produce novel bridged 2,6‐dihydroxypyran‐4‐ones (Scheme 2). The structure of the obtained compounds 6a and 7a was confirmed by X‐ray structure analysis. |
| |
| Keywords: | Fluorinated compounds 1 3 5‐Triketones Bromination Chlorination Pyran‐4‐ones Aromatization |
|
|
