The first single step regioselective formation of diazadioxacalix[4]arenes and diazadioxa[14]cyclophanes is described. These macrocycles were formed via condensation of 3- or 4- amino-phenols, with 1,5-difluoro-2,4-dinitrobenzene. Conformational properties of the macrocycles, as well as the mechanistic details leading to the observed bridging pattern where investigated.

Single step, regioselective synthesis of diazadioxacalix[4]arenes and diazadioxa[14]cyclophanes bearing an alternating N/O-bridge pattern

244th National Meeting (2012)

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