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Halogenation of Fluorinated 1,3,5‐Triketones
Author(s) -
Sevenard Dmitri V.,
Kazakova Olesya,
Chizhov Dmitri L.,
Yachevskii Danil S.,
Lork Enno,
Poveleit Jörn,
Charushin Valery N.,
Röschenthaler GerdVolker
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790043
Subject(s) - chemistry , halogenation , cyclohexanone , aromatization , phenols , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
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.