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Synthesis of an ortho-Triazacyclophane: N,N′,N′′-Trimethyltribenzo-1,4,7-triazacyclononatriene

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posted on 2010-11-19, 00:00 authored by Andria M. Panagopoulos, Matthias Zeller, Daniel P. Becker
N,N′,N′′-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald−Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the new cyclophane to have a C2-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).

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