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Communication | Regular issue | Vol 81, No. 1, 2010, pp.67-72
Published online, 26th November, 2009
DOI: 10.3987/COM-09-11854
A [2]Rotaxane Containing N,N-Dialkylammonium Ion and N-Alkylaniline Centers. Translational Isomerism, and Specific N-Acylations

Yuji Tokunaga,* Masanori Kawabata, Yuji Yamauchi, and Naoki Harada

*Department of Materials Science and Engineering, Faculty of Engineering, Fukui University, Bunkyo, Fukui 910-8507, Japan


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