Piperidinodechlorination of chloro nitro naphthalenes. Further comparison between nitro-group and aza-group activation

The importance of specific solvation (H bonding) in the nucleophilic reactions of N-heteroaromatic substrates has been stressed in recent studies and was suggested to be a major differential feature between aza- and nitro-group activation, on the basis of the solvent effects observed in the reaction of 2- and 4- chloroquinoline with piperidine. The most appropriate comparison with the latter reaction requires the investigation of the nitronaphthalene analogs, which is the object of the present note.