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Halogenation of Fluorinated 1,3,5-Triketones

✍ Scribed by Dmitri V. Sevenard; Olesya Kazakova; Dmitri L. Chizhov; Danil S. Yachevskii; Enno Lork; Jörn Poveleit; Valery N. Charushin; Gerd-Volker Röschenthaler

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
208 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

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)bis[2,2,2‐trifluoroethanones] (= 2,6‐bis(trifluoroacetyl)phenols; Scheme 4). Additionally, the 1,3,5‐triketones prepared add readily H~2~O 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.

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