Synthesis of Cavity Extended Cyclotriveratrylenes

Aromatic nucleophilic substitution reaction of cyclotriguaiacylene <b>1</b> with fluorobenzene derivatives bearing electron-withdrawing groups X (CHO, COCH<sub>3</sub>, CN, NO<sub>2</sub>) in the <i>para</i> position gives a series of cyclotriveratrylene derivatives (<b>3a</b><b>−</b><b>d</b>), where the X substituents can be transformed to hydrogen-bond donor groups to afford new CTV-based heteroditopic receptors. The substituents of compounds <b>3a</b><b>−</b><b>d</b> favor the facile demethylation reaction of the CTV derivatives. Attempts to perform alkylation reactions on derivatives (<b>8c</b>,<b>d</b>) evidenced the formation of a stereoisomeric mixture of symmetrical and unsymmetrical compounds.