Synthesis and structure of new chlorine containing calix[4]resorcinols

New calix[4]resorcinols containing four organochlorine moieties have been synthesized in high yields via one-step condensation of resorcinol, 2-methylresorcinol or pyrogallol with 4′-formylphenyl 4-(chloromethyl)benzoate. It has been found that the diastereomeric ratio of the products depends substantially on the starting polyphenol. The rctt- and/or rccc-diastereomers have been isolated and their structure and composition have been determined by ¹H, ¹³C NMR and IR spectroscopy, MALDI mass spectrometry and elemental analysis, the crystal structure of one rctt-product has been established by single crystal X-ray diffraction.