Improved Synthesis of 1-Aryl-2, 2-Dichloro-1-Alkanones

Abstract

Recently¹ we described a convenient synthesis of 1-aryl-2, 2-dichloro-1-alkanones 1 by a reaction sequence involving conversion of the parent alkylarylketones into the corresponding N-cyclohexylketimines, followed by chlorination with N-chlorosuccinimide in carbon tetrachloride to afford N-cyclo-hexyl α,α-dichloroketimines, the latter compounds being hydrolyzed in acidic medium to yield the title compounds 1. The relative inaccessibility of compounds of type 1 in the literature was striking. α,α-Dichloroacetophenones 1 (R=H) are