Synthesis and Molecular Shuttling of [2]Rotaxanes under Mild Conditions

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<jats:title>Abstract</jats:title> <jats:p>[2]Rotaxanes constructed with an ethereal end-capped axle and a dibenzo-24-crown-8 wheel were synthesized from pseudorotaxanes bearing an alcoholic terminus and diaryldiazomethanes using diphenyl phosphate as a catalyst. The reaction proceeded at room temperature in nonpolar solvents within several hours. The [2]rotaxanes thus obtained behaved as ammonium salts derived from a very strong base such as DBU. Thus, the amine form of the [2]rotaxane reacted with a weak acid, CO2–H2O, to give a hydrogencarbonate salt of the [2]rotaxane, which turned back to the amine form after drying followed by evacuation.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 42 (6), 630-632, 2013-05-18

    Oxford University Press (OUP)

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