The reactions of highly fluorinated organic compounds. Part IX. 1H-Decafluoro-4-trifluoromethylcyclohexane, nonafluoro-4-trifluoromethylcyclohex-1-ene, and perfluoro-(3-methyladipic) acid

Organic Fluorine Chemistry

“…Fluorination with elemental fluorine gave way to reactions of organic compounds with high-valency metal fluorides, which generally give higher yields. Cobalt trifluoride is now used almost exclusively, having supplanted the more expensive silver difluoride, also capable of the same reactions [86,87]. (32) CoF3…”

“…H3C-(O)-CH(CH 3h [87] The electrochemical fluorination process is especially suitable for converting compounds which are soluble in anhydrous hydrogen fluoride to perfluoro derivatives. The most useful application so far is the preparation of perfluoroacyl fluorides, which yield perfluorocarboxylic acids or their derivatives.…”

“…(181) Ct, J 100°C C5FllCI 71.2% Br2 C 5 Fll C02Ag ---SO-:=9c:..: O ' -OC' ---' t " J""' "c ",," c,',," (336] C 5Flli 73.9 % The high-temperaure chlorination and bromination of perfluoro-pcymene cleaves the carbon chain and gives 4-halogenoperfluorotoluene and perfluoroisopropyl halides [337]. (182) CI,.…”

“…(182) CI,. 540-555'C t f. p-CFaC6FlOBr 21% (337] The direction of addition of hydrogen halides to fluorinated olefins is determinated by the polarity of the double bond, which in turn depends on the position of fluorine atoms in the molecule. In 1, 1, I-trifluoropropene, halogen joins the terminal carbon atom.…”