Low temperature capture of pseudorotaxanes

Org Lett. 2011 Feb 4;13(3):458-61. doi: 10.1021/ol1027915. Epub 2011 Jan 7.

Abstract

Yields of a rotaxane can be improved by employing a two-step capture protocol. Cooling a solution of the linear and macrocyclic components required for the rotaxane increases the population of the target pseudorotaxane, which is then captured by a rapid capping reaction between an azide and PPh(3). The resulting iminophosphorane rotaxane can then be manipulated synthetically at elevated temperatures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cold Temperature
  • Models, Molecular*
  • Rotaxanes / chemical synthesis*
  • Rotaxanes / chemistry*

Substances

  • Rotaxanes