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Halogenation of fluorinated cyclic 1,3-dicarbonyl compounds: new aspects of synthetic application |
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| Authors: | Dmitri V. Sevenard,Mikhail Vorobyev,Helma Wessel,Vera Vogel,Valentine G. Nenajdenko,Gerd-Volker Rö schenthaler |
| Affiliation: | a Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstr. 1, 28359 Bremen, Germany b Department of Chemistry, Ural State University, Lenina 51, 620083 Ekaterinburg, Russian Federation c Institute of Inorganic and Physical Chemistry, University of Bremen, Leobener Str., 28334 Bremen, Germany d Department of Chemistry, Moscow State University, 119899 Moscow, Russian Federation |
| Abstract: | In order to elaborate on an approach towards 2-(fluoroacyl)phenols being the superior alternative to the conventional Fries-rearrangement based methodology, the behaviour of cyclic fluorinated 1,3-dicarbonyls in reactions with halogenating agents was examined. The synthetic relevance of the polyhalogenated compounds obtained was demonstrated by the synthesis of several new heterocycles. An aromatization via a halogenation-dehydrohalogenation sequence proved to be a rewarding synthetic route to 2-(fluoroacyl)phenols and previously unknown 3-(fluoroacyl)thiochromones. The structure of one of the synthesized compounds was confirmed by X-ray diffraction analysis. |
| Keywords: | Fluorinated compounds Phenols Thiochromones 1,3-Dicarbonyl compounds Halogenation |
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