Diazadioxacyclophanes

Abstract

Six new cyclophane molecules (5-10) were synthesized from alpha,alpha'-bis(N-tosyl-4-aminophenyl)-1,4-diisopropylbenzene and alpha,alpha'-bis[4-(n-bromoalkyloxy)phenyl]-1,4-diisopropylbenzene. The crystal and molecular structures of alpha,alpha'-bis(4-aminophenyl)-1,4-diisopropylbenzene (3), alpha,alpha'-bis (N-tosyl-4-aminophenyl)-1,4-diisopropylbenzene 4 and the ditosyl derivative of the diazadioxacyclophane 6 were determined. The noncyclic compounds 3 and 4 display the ami conformation. Diazadioxacyclophane 6 possesses a central cavity that might be exploited to accommodate guest molecules, but some conformational change would probably be required.