2,2,2-Trifluoroethylarenes were obtained in good yield from the addition of KF to 2′,2′-difluorostyrenes in the presence of crown ether. A linear regression line obtained from correlation between log(reaction rate) and Hammett constants with slope of +4.28 suggested that this addition process is very sensitive to the substituents on the phenyl ring.
References
1.
Organofluorine Chemistry, Principles and Applications; BanksR. E., SmartB. E., TatlowJ. C., Eds.; Topics in Applied Chemistry, Plenum: New York, 1994.
2.
FillerR., KobayashiY., Eds.; Biomedical Aspects of Fluorine Chemistry; Kodansha Ltd.: Tokyo, 1982.
3.
OberhammerH., J. Fluorine Chem., 1983, 23, 147.
4.
BanksR.E. (ed.). Organofluorine Chemicals and Their Industrial Applications.Ellis Haywood, Chichester, 1979.
5.
BanksR.E., Preparation, Properties and Industrial Applications of Organofluorine Compounds, Ellis Haywood, Chichester, 1982.
6.
(a) ParatianJ.M., LabbeE., SibilleS., and PerchonJ., J. Organomet. Chem., 1995, 137.
7.
BurgessD.A., FinnM. F., JordanD., RaeI. D., and BarryD., Aust. J. Chem., 1984, 1769.
8.
ClarkJ.H., McClintonM. A., and BladeR. J., J. Fluorine. Chem., 1992, 32, 257.
9.
FuquaS.A., DuncanW. G., and SilversteinR. M., J. Org. Chem., 1965, 30, 1027.
10.
DuanJ.-X., and ChenQ.-Y., J. Chem. Soc. Perkin Trans. 1; 1994, 725.
11.
AndoA., MikiT., KumadakiI., J. Org. Chem., 1988, 53, 3637.
12.
KondratenkoN.V., VechirkoE. P., YagupolskiiL. M., Synthesis, 1980, 11, 932.
