α,α,α,ω-Tetrachloro- andα,α,α-trichloroalkanes are capable of addition to olefins through rupture of the C-Cl bond in the CCl3 group during which 40–55% yields are formed of adducts with the structure RCHClCH2CCl2 (CH2)nX (X=H or Cl). The reaction takes place in propanol at 135° in the presence of 1.5 mole% of Fe(CO)5. The addition of 1,1,1,3-tetrachloropropane has also been accomplished under the same conditions, but in methanol or ethanol.
Isopropyl and benzyl alcohols reduce the CCl3 group in polychloroalkanes to a CHCl2 group. The reaction takes place in the presence of catalytic quantities of Fe(CO)5 at 145° with a yield of 50–65%.
In the addition and reduction reactions of polychloroalkanes investigated, which were carried out in isopropyl alcohol, the latter undergoes various transformations with the formation of propylene, isopropyl chloride, diisopropyl ether, and acetone.
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Chukovskaya, E.T., Kuz'mina, N.A. & Freidlina, R.K. A new reaction of the CCl3 group in polychlorohydrocarbons. Russ Chem Bull 19, 2200–2205 (1970). https://doi.org/10.1007/BF00861496