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The 1,3-cycloaddition of azides to terminal alkynes has previously been employed to prepare rotaxanes and polyrotaxanes by using cucurbituril to accelerate the reaction by organizing the reactants and increasing their effective molarity: (a) Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302-5308.
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0001603015
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The uncatalyzed 1,3-cycloaddition between azides and electron-poor internal alkynes has been used to form rotaxanes by a "threading-followed- by-stoppering" protocol: (e) Ashton, P. R.; Clink, P. T.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem.-Eur. J. 1996, 2, 729-736.
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33644527707
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note
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6 proceeds via single copper atom intermediates, binuclear species, or structurally more complex aggregates. Further studies are ongoing.
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23
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(b) Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z.; Walker, D. B. Angew. Chem., Int. Ed. 2005, 44, 4557-4564.
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