Ozonolysis of olefins containing monochloro substituted double bonds

Abstract

Ozone cleavage of 12 substituted vinyl chlorides (1) in methanol occurred such that the chlorinated moiety of the double bond afforded the carbonyl fragment (i.e. acyl chloride) and the nonchlorinated moiety afforded the carbonyl oxide fragment. All of these fragments underwent secondary reactions: formyl chloride gave carbon monoxide and hydrogen chloride; all other acyl chlorides yielded the corresponding methyl esters. The carbonyl oxides were converted into the corresponding methoxy hydroperoxides. Under the influence of hydrochloric acid unsubstituted and monosubstituted methoxy hydroperoxides were dehydrated to form the corresponding methyl esters, whereas the disubstituted methoxy hydroperoxide of acetone produced the cyclic trimeric peroxide of acetone.