Peroxide Induced Addition Reaction of Aliphatic Alcohols to Tetrachloroethylene

Abstract

Addition reactions of aliphatic alcohols to tetrachloroethylene using organic peroxides, as an initiator yielded 1: 1-adducts and the corresponding unsaturated compounds. Their yields, in general, were found to be lower than those observed previously for the reactions initiated by r-ray.
The saturated chlorine-containing alcohols thus obtained were acetylated in yields from 62 to 89%. The yields decreased in the order:
Isopropyl>Ethyl, Methyl>n-Propyl
Behavior of the acetates of the ethanol-adduct and the corresponding unsaturated compound towards treatment with bromine under UV-irradiation was also examined. A monobrominated compound was obtained in 61% yield from the acetate of the saturated adduct. From the unsaturated acetate, another bromine adduct was obtained in 65% yield. Synthesis of Oxygen-containing Halogenated Compounds. V.