51760-82-8Relevant academic research and scientific papers
Chemoselective halogenation of 2-hydroperfluoroalkyl aldehydes
Wiebe, Donald A.,Burton, Donald J.
, p. 4 - 11 (2012/07/13)
2-Hydroaldehydes, RfCH(R)CHO, where Rf = CF 3, C2F5, n-C3F7 and R = CF3, C2F5, n-C3F7, Ph, H, were prepared via acid hydrolysis of the corresponding vinyl ethers, R fC(R) = CHOCH3, which can be readily prepared by reaction of Ph3P+C?HOCH3 with the corresponding ketone. The 2-hydroaldehydes can be chemoselectively converted to the acyl halide, RfCH(R)C(O)X (X = Cl, Br), via free-radical halogenation. The perfluoroalkyl group deactivates the 2-position toward radical abstraction of the 2-hydrogen, and halogenation occurs exclusively at the formyl hydrogen. However, halogenations of the 2-hydroaldehydes in glacial acetic acid chemoselectively gives the 2-haloaldehydes, RfCX(R)CHO, X = Cl, Br. Hydrolysis of the 2-hydroperfluoroacyl halides provides a useful route to 2-hydroperfluoroalkyl branched carboxylic acids, useful ketene precursors. This route avoids the use of toxic fluoroolefins, such as perfluoroisobutylene.
New practical synthesis of panomifene. The effect of 2-trifluoromethyl substituent on the stereoselectivity of dehydration of 1,1,2-triarylethanols
Nemeth, Gabor,Kapiller-Dezsofi, Rita,Lax, Gyoergyi,Simig, Gyula
, p. 12821 - 12830 (2007/10/03)
Highly stereoselective eliminations were achieved by acid-catalysed dehydration of 1-(4-alkoxy)-3,3,3-trifluoro-1,2-diphenylpropan-1-ols (10, 11, 15). The influence of the trifluoromethyl group on the stereochemistry of the elimination has been discussed. The observed high stereoselectivity has been applied to give a new, practical synthesis of antiestrogenic drug panomifene (1).
A novel access to 4-fluoropyrimidines from α-chloro-α'-trifluoromethylketones
De Nanteuil
, p. 2467 - 2468 (2007/10/02)
When treated with formamidine acetate and KOH, α-chloro-α'-trifluoromethyl ketones afford, though in moderate yield, 4-fluoropyrimidine derivatives.
