Jump to main content
Jump to site search

Issue 4, 2015
Previous Article Next Article

Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction

Author affiliations

Abstract

We recently identified competitive formation of doubly interlocked [3]rotaxanes as the origin of the non-linear variation in yield of [2]rotaxane with macrocycle size in the bipyridine-mediated AT-CuAAC reaction. Selection of reaction conditions gave [2]rotaxanes in essentially quantitative yield in all cases and hard to access doubly threaded [3]rotaxanes in up to 50% yield in a single, four component coupling. Based on the effect of macrocycle structure on the reaction outcome we propose a detailed mechanism of [3]rotaxane formation.

Graphical abstract: Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Dec 2014, accepted on 03 Feb 2015 and first published on 03 Feb 2015


Article type: Edge Article
DOI: 10.1039/C4SC03999H
Citation: Chem. Sci., 2015,6, 2398-2404
  • Open access: Creative Commons BY license
  •   Request permissions

    Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction

    E. A. Neal and S. M. Goldup, Chem. Sci., 2015, 6, 2398
    DOI: 10.1039/C4SC03999H

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements