Reaction of Organic Compounds with the System SF4-HF-Halogenating Agent. XII. Reactions of Aliphatic Alcohols with the System SF4-HF-Cl2
Reactions of aliphatic alcohols with the system SF4-HF-Cl2 are investigated. Chlorofluoroalkanes are shown to be produced in high yields when the double bond formation occurs under mild conditions.
Kunshenko,Ostanin,Yagupol'skii
p. 1420 - 1423
(2007/10/03)
REACTION OF ORGANIC COMPOUNDS WITH SF4-HF-HALOGENATING SYSTEM VII. REACTIONS OF OLEFINS WITH THE SF4-HF-Cl2(Br2) SYSTEM
Under the influence of the SF4-HF-Cl2(Br2) system halogen-containing olefins undergo conjugate halogenofluorination.It was shown for the case of (Z)- and (E)- 1,2-dichloroethenes that these reactions take place anti-stereospecifically through the formation of the bromonium ions.The accumulation of chlorine atoms in the olefin molecule hinders electrophilic addition of stoichiometric equivalents of ClF and BrF at the double bond.The SF4-HF-Br2 system is an effective agent for substitutive fluorination of organic compounds containing bromine.Only the bromine atoms situated at the secondary carbon atom are substituted by fluorine.
Kunshenko, B. V.,Mokhamed, Nagib Mukhtar,Omarov, V. O.,Muratov, N. N.,Yagupol'skii, L. M.