Reactivity of n-aryl-α, α-dichlorinated arylketimines

N-Aryl-α,α-dichloroalkylarylketimines are formed from N-aryl-alkylarylketimines with N-chloro succinimide in carbon tetrachloride. Reaction of N-1-(2,2-dichlor-1-arylpropylidene)anilines with sodium methoxide the latter compounds formally involves migration of the notrogen atom from the 1- to the 3-position. The reaction of higher substituted N-aryl-α,α-dichloroalkylarylketimines with sodium methoxide leads mainly to α-chloro-α,β-unsaturated ketones. In the case of long-chain α,α-dichloroketimines, a formal γ-functionalization was observed. The reaction mechanisms are discussed in detail.