An ortho-Directing Effect in the Nucleophilic Aromatic Substitution Reactions of Primary and Secondary 2,4-Dichloro- and 2,3,4- Trichlorobenzamides with Ethanethiolate.

Abstract The reactions of the primary amide and several secondary amides of 2,4-dichloro- and 2,3,4-trichlorobenzoic acid with potassium ethanethiolate in DMF were observed to proceed with a remarkable degree of ortho-regioselectivity. This effect was found to be absent using related tertiary amides as substrates.