A 2ROTAXANE CONTAINING N,N-DIALKYLAMMONIUM ION AND N-ALKYLANILINE CENTERS. TRANSLATIONAL ISOMERISM, AND SPECIFIC N-ACYLATIONS

摘要

This paper describes the molecular shuttling and specific N-acylationsof a [2]rotaxane featuring an encircling crown ether unit and both N-alkylanilineand N,N-dialkylamine centers on its dumbbell-shaped component. The crownbinds predominantly to the dialkylammonium center under neutral conditions.Reactions with acid anhydride in nonpolar solvents and in the absence orpresence of a weak base resulted in the N-acylations occurring mainly at theaniline moiety, and selective N-acylations of the dialkylamine unit occurred inpolar solvents in the presence of strong bases.