Highly efficient synthesis of rotaxane assisted by preorganisation of pseudorotaxane using bis(crown ether)s
SupramolChem_22_815.pdf 281 KB
The tether-assisted synthesis of rotaxane by olefin metathesis has been studied in detail. Bis(crown ether)s, in which two crown ethers are connected by a linker, were threaded onto ammonium salts bearing a terminal olefin to form pseudorotaxanes. The pseudorotaxanes were converted into tethered rotaxanes in the presence of Grubbs catalyst, followed by removal of the linkers to produce rotaxanes in excellent yields. Preorganisation of the two reactive ends has led to a great improvement in the yield of rotaxanes. The ring strain of the tethered rotaxanes and the flexibility of the pseudorotaxanes were responsible for the formation of the tethered rotaxanes.
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Copyright (c) 2010 Taylor & Francis. This is an electronic version of an article published in "Supramolecular Chemistry, Volume 22, Issue 11 & 12 November 2010, pages 815 - 826" Disability and Rehabilitation is available at: http://dx.doi.org/10.1080/10610278.2010.514611