Summary
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1.
Treatment of 1,1,3,3,3-pentafluoropropene and of hexafluoropropene with aluminum chloride in CH3COCl or CHCl3 solution in the cold effects smooth replacement of fluorine by chlorine atoms with formation of CCl3--CH=CCl2 and CCl3-CF=CCl2, respectively.
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2.
The ready replacement of fluorine by chlorine atoms in these compounds is the result of the conjugation of bonds, which leads to mobility of fluorine atoms in the CF3 group and to ready allyl rearrangement.
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Literature cited
A. H. Henne and M. S. Newmann, J. Amer. Chem. Soc. 60, 1697 (1938).
W. T. Miller, Ed. W. Faqer, and P. H. Criswald, J, Amer. Chem. Soc. 82, 705 (1950).
J. H. Simons (Editor), Fluorine Chemistry, Vol. 1 (Russian translation), Foreign Lit. Press, Moscow, 1953.
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Sterlin, R.N., Sidorov, V.A. & Knunyants, I.L. Reactions of fluoro olefins Communication 9. Action of anhydrous aluminum chloride on fluoro olefins. Russ Chem Bull 8, 55–57 (1959). https://doi.org/10.1007/BF00914214
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DOI: https://doi.org/10.1007/BF00914214