Magic Ring Rotaxanes by Olefin Metathesis†
Andreas F. M. Kilbinger Dr.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorStuart J. Cantrill Dr.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorAndrew W. Waltman
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorMichael W. Day Dr.
Beckman Institute, X-Ray Crystallography Laboratory, California Institute of Technology, Pasadena, CA 91125, USA
Search for more papers by this authorRobert H. Grubbs Prof.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorAndreas F. M. Kilbinger Dr.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorStuart J. Cantrill Dr.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorAndrew W. Waltman
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorMichael W. Day Dr.
Beckman Institute, X-Ray Crystallography Laboratory, California Institute of Technology, Pasadena, CA 91125, USA
Search for more papers by this authorRobert H. Grubbs Prof.
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA, Fax: (+1) 626–564–9297
Search for more papers by this authorA.F.M.K. thanks the Alexander von Humboldt Foundation for a Feodor–Lynen Research Fellowship. We thank Dr. Mona Shahgholi for performing the mass spectrometric analyses, Dr. Jennifer Love for assisting with initial NMR spectroscopic measurements, and Dr. Steven Goldberg for valuable comments regarding this manuscript.
Graphical Abstract
Trick or treat? Ruthenium alkylidene catalyzed ring-closing metathesis of crown ether like diene substrates around a dumbbell-shaped secondary ammonium ion affords [2]rotaxanes. The reversible nature of this process has been demonstrated through a “magic ring” synthesis, wherein the preformed olefinic macrocycle and dumbbell-shaped component equilibrate to form the hydrogen-bond-stabilized [2]rotaxane in the presence of a metathesis catalyst (see scheme).
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- 28CCDC 188147 (11⋅PF6) and CCDC 188995 (12⋅PF6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or [email protected]). Structure factors are available from the authors via email:[email protected].
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