An umpolung of Lewis acidity/basicity at nitrogen by deprotonation of a cyclic (amino)(aryl)nitrenium cation

Jiliang Zhou, Liu Leo Liu, Levy L. Cao, Douglas W. Stephan
2018 Chemical Communications  
The cyclic (amino)(aryl)nitrenium cation 2 is Lewis acidic at nitrenium N1, reacting with PMe3 affording a Lewis acid/base adduct 3, while deprotonation of 2 provides the neutral compound 4 which is Lewis basic at N1.
doi:10.1039/c8cc01331d pmid:29527605 fatcat:vtyass5m5jddxnehf4g3p22sz4