Synthesis of resorcin[4]arene bearing self-folding substituent

Thiomethylation of resorcin[4]arene using N,N-diisopropyl-2-aminoethanethiol hydrochloride and formaldehyde [1:4:4 molar ratio] carried out in methanol/acetic acid [1:1 v/v] at 60 °C produced monofunctionalized product 3 in 68% yield. The introduced substituent was intramolecularly self-included into the cavity. This self-inclusion reduced the reactivity of the aromatic rings and inhibited further functionalization.