Synthesis of functionalized oxacalix[4]arenes

Tetranitrooxacalix[4]arenes are generated in high yield by the room-temperature SNAr reaction of 1,3-dihydroxybenzenes with 1,5-difluoro-2,4-dinitrobenzene. The reaction is tolerant to a range of functionality on the nucleophilic component, including hydroxyl-substitution at the 2- and 5-positions, which yields previously unknown 26,28- and 5,17-dihydroxyoxacalix[4]arenes.