Dialkylamino and trialkylammonium groups in close proximity: intra- and intermolecular ways of formation, structural consequences, and properties. A case of metal-free directed ortho alkylation

Abstract

Pyrrolidino-functionalised 1,8-bis(dialkylamino)naphthalenes undergo mild peri-quaternisation, either intra- or intermolecularly, resulting in both stable quaternary salts with peri-situated dialkylamino and trialkylammonium groups and their reactive transient variants. For the first time, structural information, and physicochemical properties of these sterically hindered and virtually unexplored molecules have been revealed including the first examples of metal-free directed ortho alkylation.