The Chlorination of Vinyl Compounds in Alcohols

Article abstract of DOI:10.1246/bcsj.61.4393

Upon the chlorination of vinyl compounds in alcohols, the reaction products were composed of 2-alkoxy-1-chloro compound (A), 1-alkoxy-2-chloro compond (B) and vicinal dichloride (C).Various vinyl compounds were chlorinated in alcohols at 40 deg C in order to elucidate the effect of their molecular structure on the product distribution.The A/(A+B) was inversely proportional to the relative rate of ordinary chlorination in carbon tetrachloride.The A/(A+B) for the chlorination of allyl chloride in methanol was little affected by the reaction conditions: (1) reaction temperature, (2) mole ratio, and (3) elapse of time.However, the A/(A+B) increased with increasing E_s value of the alkyl group of alcohol.