A simple and scalable synthesis of 2,14-dithiacalix[4]arene with alternating bridges (-CH2- and -S-) is reported. Proper selection of the bisphenol-based starting building blocks can provide not only the title compound (58%) but also yet unreported homooxa analogues possessing three different bridging units (-CH2-, -S- and -CH2-O-CH2-) in the molecule. These systems exhibit interesting conformational behaviour allowing for the study of flip-flop motion of the circular hydrogen bond arrays using dynamic NMR techniques.

Department of Organic Chemistry Institute of Chemical Technology Prague Technicka 5 166 28 Prague 6 Czech Republic

References provided by Crossref.org

Synthesis of Monothiacalix[4]arene Using the Fragment Condensation Approach

Breaking thiacalix[4]arene into pieces - a novel synthetic approach to higher calixarenes bearing mixed (-S-, -CH2-) bridges