Aromatic Monocarbonylpolyfluoro-compounds

Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone

“…The Lewis acid properties of Al 2 O 3 suggest that the transformation of 2 into 3 requires acid catalysis. This is also confirmed by reports in the literature, [19] where concentrated H 2 SO 4 is used for the transformation of 2-aminobenzophenones into the corresponding acridines. Thus, ortho-substituted derivatives 2a-e were firstly treated with concentrated H 2 SO 4 .…”

“…Indeed it is reported that nucleophilic attack to the carbonyl function causes haloform-type degradation of the ketone, affording pentafluorobenzene and perfluorinated aromatic carboxylic acids. [19] We performed a detailed study on 2a to optimize the experimental conditions for its transformation into the corresponding acridone. We obtained the best results when using 1 equiv.…”

“…IR spectra were obtained with a Spectrum 100, FTIR Spectrometer PerkinElmer. NMR spectra were recorded in CDCl 3 with a Varian Mercury 400 Spectrometer ( 1 H 400 MHz, 13 C 100 MHz, 19 F 376 MHz). Molecular structures and purity were analyzed by GC-MS (GCD 1800C; Hewlett-Packard) with a 50-m DB-5MS column (J&W Scientific, Folsom, Calif.).…”

“…On the other side, ortho-substituted nonafluorobenzophenones obtained in that way could be useful reagents, for instance, for the synthesis of N-arylocta- fluoroacridones by an intramolecular aromatic nucleophilic reaction; unfortunately, that approach is strongly hindered by haloform-type degradation that this ketone undergoes under basic conditions, producing pentafluorobenzene and pentafluorobenzoic acid. [19] Here we have investigated in more detail the reactivity of 1 with aromatic amines and we report on the possibility to exploit o-anilino-substituted nonafluorobenzophenones 2 as starting materials for the orthogonal synthesis of 9-pentafluorophenyl-1,2,3,4-tetrafluoroacridines (3) and octafluoroacridones (4) just acting on experimental conditions (Scheme 1).…”

Synthesis and structure of fluorophenyl derivatives of the 10-vertex monocarbaborane anions [1-CB9H10]− and [2-CB9H10]−

“…At the first step we tried reaction of decaborane with C 6 F 5 CHO in alkaline aqueous ethanol. Unfortunately, no formation of carborane species was observed, that could be explained by formation of stable pentafluorobenzaldehyde hemiacetal [16]. Similarly, no carborane formation was found in the case of reaction with trifluoroacetaldehyde monohydrate.…”