Of fluoroketones

Reactions of Organic Fluorine Compounds Table 14. Reactions of Fluoroketones with Nucleophiles... 

Fluorination of an enamine, enol ether, or enol acetate with CF3OF gave 60-70% yields of fluoroketone (708). Bromination of an endiamine gave the bis-imonium salt (647). 

Stabilisation of the tetrahedral forms of fluoroalkyl ketones The presence of a fluoroalkyl group in a position of a carbonyl strongly enhances its electrophilicity, and hence its reactivity, towards nucleophiles. The anionic tetrahedral intermediates are stabilised by the electron-withdrawing group Rf (Fig. 20) [69,70]. This phenomenon is illustrated by the ability of fluoroketones to afford stable hydrates in aqueous medium. 

Ab initio calculations have been performed to evaluate the ease of hydration and the charge densities of the carbonyl of fluoroketones that are carboxyesterase... 

HDACs are zinc metalloproteases involved in the acetylation of histone. Inhibition of HDACs represents a new strategy in human cancer therapy since these enzymes play a fundamental role in regulating gene expression and chromatin assembly. Along this line, inhibition of HD AC by fluoroketones has been studied. The inhibition power of fluoroketones toward HDACs is comparable to that of hydroxamates, which are the classical inhibitors of metalloproteases. These fluoroketones exhibit antiproliferative activities on tumor cell lines (Figure 7.44). ... 

Asymmetric fluorination of the lithium enolate derived from tetralone 307 has been achieved with several new chiral A-fluoro-l,2-benzothiazine reagents (Scheme 44) <2000JOC7583, 2000CPB1954, see also 1999JFC(97)65>. For instance, sulfonamides 149 and 150 afford the opposite enantiomers of fluoroketone 308 in up to 79% yield and 62-70% ee. 

The strong inductive effect of fluoroalkyl groups has a corresponding additive acidifying effect on alcohols (Table 4.2). For instance, perfluoro-t-butanol is of the same order of acidity as acetic acid. The hydrates of fluoroketones are also remarkably acidic [10]. 

---