89176-05-6

Upstream product

• 354-64-3 Pentafluoroethyl iodide 
• 80783-99-9 N-methoxy-N-methylcinnamamide 
• 354-33-6 1,1,1,2,2-pentafluoroethane 
• 103-26-4 Methyl cinnamate 
• 378-75-6 perfluoropropionic acid methyl ester 
• 103-64-0 bromostyrene 
• 64511-21-3 1,1,1,2,2-pentafluoro-5-phenylpentan-3-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 90550-19-9 1,1,1,2,2-pentafluoro-5-phenylpentan-3-ol 
• 89175-98-4 diethyl 3,3,4,4,4-pentafluoro-2-(methylimino)butanephosphonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 64511-21-3 1,1,1,2,2-pentafluoro-5-phenylpentan-3-one 
• 90550-19-9 (S)-1,1,1,2,2-Pentafluoro-5-phenyl-pentan-3-ol 

Relevant academic research and scientific papers

Pentafluoroethylation of Carbonyl Compounds by HFC-125 via the Encapsulation of the K Cation with Glymes

A simple protocol to overcome the explosive pentafluoroethylation of carbonyl compounds by HFC-125 is described. The use of potassium (K) bases with triglyme or tetraglyme as a solvent safely yields the pentafluoroethylation products in good to high yield

Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines

The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.

Dehydrogenation of perfluoroalkyl ketones by using a recyclable oxoammonium salt

A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+BF4-, Bobbitt's salt, 1) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1a), can easily be recovered and used to regenerate the oxoammonium salt. The dehydrogenation of perfluoroalkyl ketones by using an oxoammonium salt is reported. The reaction proceeds under mildly basic conditions and affords α,β-unsaturated products in fair to excellent yields. The reaction likely proceeds through a two-step sequence. The spent oxidant can easily be recovered and used to regenerate the oxoammonium salt. Copyright

Synthesis of medicinally interesting polyfluoro ketones via perfluoroalkyl lithium reagents

(Chemical Equation Presented) The addition of (pentafluoroethyl)- and (heptafluoropropy-1)lithium to various acyl derivatives was studied. Weinreb and morpholine amides led to polyfluoro ketones in high to quantitative yields in short reaction times. Derivatives of 2-fluorocarboxylic acids may produce 1,1,1,2,2,4-hexafluoro ketones and 1,1,1,2,2,3,3,5-octafluoro ketones. The methodology can provide inhibitors for various lipolytic enzymes, including phospholipase A2.

DIASTEREOSELECTIVE REDUCTION OF PERFLUOROALKYLATED α,β-UNSATURATED KETONES WITH BAKER'S YEAST

The differentiation of a fluorinated group in the molecule with active fermenting yeast and the double asymmetric induction in some perfluoroalkylated α,β-unsaturated ketones are described.

NOVEL SYNTHESIS OF F-1-ALKENE-1-PHOSPHONATE DERIVATIVES FROM F-ALKANOYL CHLORIDES AND THEIR EFFICIENT USE FOR PREPARING FLUORO-α,β-ENONES

(Z)-1--F-1-alkene-1-phosphonates were synthesized in good yields from F-alkanoyl chlorides and triethyl phosphite, and were proved to be useful precursors for the preparation of fluoro-α,β-enones.