Synthesis of macrocyclic polyethers via Ru complex-catalyzed metathesis cyclization and their use as the ring component of rotaxanes

Abstract

Ring closing metathesis of the vinyl group-terminated oligoethers catalyzed by RuCl 2( CHPh)(PCy 3) 2 yielded macrocyclic polyethers containing vinylene group. The 1H and 13C NMR spectra indicated the presence of C C double bond ( trans/ cis = ca. 80:20). The obtained 23-membered cyclic ether reacted with benzyl(anthrylmethl)ammonium hexafluorophosphate to produce the pseudo-rotaxane as colorless crystals. X-ray crystallography revealed N–H⋯O hydrogen bonds and stacking of the aromatic planes between the host and guest molecules, which stabilized the rotaxane structure in the solid state.