Comparative reactivity of substituted 4-nitrobenzylidene dichlorides with alkali
Abstract
A comparative study of the reactions of substituted 4-nitrobenzylidene dichlorides ArCHCl2(Ar = 3-Cl-4-NO2C6H3, 2-Cl-4-NO2C6H3, 4-NO2C6H4, 3,5-Me2-4-NO2C6H2, and 2-Me-4-NO2C6H3) with aqueous alcoholic alkali shows that chlorine substitution enhances the electron-transfer-radical mechanism, whereas methyl substitution favours the solvolysis pathway. Changes in reactivity and mechanism are discussed.