Synthesis of p-tert-butylthiacalix[4]arene with spatially separated phosphoryl and amino groups

Abstract

The reactions of p-tert-butylthiacalix[4]arenes containing phthalimide fragments with diethyl-[(p-toluenesulfonyl)oxymethyl)]phosphonate were used to synthesize new phosphonate derivatives in the 1,3-alternate configuration. Hydrolysis and hydrazinolysis of the products gave the corresponding amido- and aminophosphonate thiacalixarene derivatives. ¹H–¹H NOESY NMR spectroscopy established a 1,3-alternate configuration of the synthesized macrocycles with spatially separated phosphoryl and amino groups.