Highly efficient synthesis of [3]rotaxane assisted by preorganisation of pseudorotaxane using bis(crown ether)s

Iwamoto Hajime

Yawata Yukimi

Fukazawa Yoshimasa

Haino Takeharu

Supramolecular Chemistry

The tether-assisted synthesis of [3]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 [3]rotaxanes in excellent yields. Preorganisation of the two reactive ends has led to a great improvement in the yield of [3]rotaxanes. The ring strain of the tethered rotaxanes and the flexibility of the pseudorotaxanes were responsible for the formation of the tethered rotaxanes.

[3]rotaxane

preorganisation

bis(crown ether)

olefin metathesis

Chemistry [ 430 ]

eng

Taylor & Francis Ltd

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

[ISSN] 1061-0278

[DOI] 10.1080/10610278.2010.514611

[NCID] AA1100053X

[DOI] http://dx.doi.org/10.1080/10610278.2010.514611