1464148-90-0Relevant academic research and scientific papers
Spontaneous Assembly of Rotaxanes from a Primary Amine, Crown Ether and Electrophile
Fielden, Stephen D. P.,Leigh, David A.,McTernan, Charlie T.,Pérez-Saavedra, Borja,Vitorica-Yrezabal, I?igo J.
, p. 6049 - 6052 (2018)
We report the synthesis of crown ether-ammonium, amide and amine [2]rotaxanes via transition state stabilization of axle-forming reactions. In contrast to the two-step "clipping" and "capping" strategies generally used for rotaxane synthesis, here the components assemble into the interlocked molecule in a single, reagent-less, step under kinetic control. The crown ether accelerates the reaction of the axle-forming components through the cavity to give the threaded product in a form of metal-free active template synthesis. Rotaxane formation can proceed through the stabilization of different transition states featuring 5-coordinate (e.g., SN2) or 4-coordinate (e.g., acylation, Michael addition) carbon. Examples prepared using the approach include crown-ether-peptide rotaxanes and switchable molecular shuttles.
Sodium ions template the formation of rotaxanes from BPX26C6 and nonconjugated amide and urea functionalities
Lin, You-Han,Lai, Chien-Chen,Liu, Yi-Hung,Peng, Shie-Ming,Chiu, Sheng-Hsien
supporting information, p. 10231 - 10236 (2013/10/21)
Picking up the thread: The macrocycle bis-p-xylyl[26]crown-6 is capable of forming pseudorotaxane-like structures with single, nonconjugated urea or amide moieties when assisted by templating Na+ ions (see example). By using this approach, rotaxanes were synthesized with glycine residues or the repeating unit of nylon-6,6 as key components in the threadlike units. Copyright
