128746-91-8Relevant articles and documents
FLUORINATED ACETYLENES. PART 7. PREPARATION AND SOME REACTIONS OF 4,4,4-TRIFLUOROBUT-2-YNOIC ACID AND 1-PHENYL-4,4,4-TRIFLUOROBUT-2-YN-1-OL
Tajammal, Sabiha,Tipping, Anthony E.
, p. 45 - 57 (1990)
Treatment of the salt CF3C CLi with alkyl chloroformates affords the compounds CF3C CCO2R (R=Et and CH2Ph) in relatively low yield and with gaseous carbon dioxide yields the acid CF3C CCO2H.Reaction of the acid with diazomethane gives the methyl ester which, with an excess of the reagent, undergoes regiospecific 1,3-dipolar cycloaddition to produce 3-carbomethoxy-4-trifluoromethylpyrazole and hence the 3- and 5-carbomethoxy-1-methyl-4-trifluoromethylpyrazoles.Oxidation of the alcohol CF3C CCH(OH)Ph (active MnO2) affords a 70:23 mixture of 3-benzoyl-2,4-bis(trifluoromethyl)-2-hydroxy-6-phenyl-α-pyran and E-1,3-dibenzoyl-2-trifluoromethylpropene (via the ketone CF3C CCOPh).
(E)-1,3-Dibenzoyl-2-trifluoromethylpropene and 3-Benzoyl-6-phenyl-2,4-bis(trifluoromethyl)-2H-pyran-2-ol: Novel Products from the Oxidation of 1-Phenyl-4,4,4-trifluorobut-2-yn-1-ol with Active Manganese(IV) Oxide
Pritchard, R. G.,Tajammal, S.,Tipping, A. E.
, p. 294 - 297 (2007/10/02)
Comparison of the two benzoyl groups attached to the ends of the propene chain reveals a slight shrinkage in the linking C-C bond when the group is conjugated to the propene double bond .However, this is not reflected in the double bond itself, which at 1.312 (7) Angstroem is extremely short.In the substituted pyran, the benzoyl group has been forced out of conjugation by steric congestion but in this case too, even though the adjacent double bond is able to conjugate within the pyran ring, it still retains full double-bond character .Intermolecular hydrogen bonds between the benzoyl O atom and the alcohol group link the pyran molecules into infinite chains along a.