Feet-to-Feet Connected Trisresorcinarenes

Org Lett. 2020 Jan 17;22(2):352-356. doi: 10.1021/acs.orglett.9b03693. Epub 2019 Nov 21.

Abstract

The macrocyclization of resorcinol and odd-numbered bisdioxolanes under acidic conditions produced feet-to-feet connected trisresorcinarenes possessing three resorcinarene units linked with odd-numbered alkyl chains. The formation of trisresorcinarenes was confirmed using high-resolution mass spectrometry and NMR spectroscopy. The trisresorcinarenes were isolated as protected forms in moderate yields. The protected trisresorcinarenes exhibited D3h symmetry in conformation in solution. Crystal structure analysis revealed that the protected trisresorcinarenes possess large inner spaces surrounded by three resorcinarene units.