The missing member of the partially O-alkylated resorcinarene family: synthesis and conformation of methyl tetramethoxy resorcinarene

Org Lett. 2013 Mar 1;15(5):1096-9. doi: 10.1021/ol400118t. Epub 2013 Feb 18.

Abstract

An improved Lewis acid catalyzed synthesis method for methyl tetramethoxy resorcinarene is described, which produced the missing lower rim methyl derivative of this partially O-alkylated resorcinarene family. Structural characterization by means of variable temperature NMR experiments and single crystal X-ray diffraction studies furthermore revealed that the resorcinarene core adopts different conformations in the solid state and in solution.