Preparation of Pillararene-Based Rotaxanes from Acyl Chlorides and Amines
European Journal of Organic Chemistry, Wiley, 2015/2015/3/479-485
Pillararene-based rotaxanes have been prepared from the reactions of diacyl chloride reagents with various amine stoppers. The yields of the rotaxanes are sensitive to the reaction conditions (solvent and stoichiometry) as well as to structural and electronic factors. In particular, the nature of the starting amine reagent has a dramatic influence on the yields of rotaxanes; thus, the reaction outcome is not simply related to the binding constant of the diacyl chloride reagent with the pillararene. Indeed, the differences in the yields must be related to the different affinities for the various monoacylated intermediates. The yields of the rotaxanes are also influenced by several structural factors such as the chain length of the diacyl chloride reagent and the size of the peripheral substituents of the pillararene building block. Finally, the preparation of rotaxanes from alkyldiamine reagents and acyl chloride stoppers has also been investigated.
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