Triptycene-Based Macrocycles

Significance

The authors report the synthesis of three pairs of novel triptycene-based expanded oxacalixarenes by the S_N2 reactions of 2,7-dihydroxytriptycene with 2,3,5,6-tetrachloropyridine, 1,5-difluoro-2,4-dinitrobenzene and cyanuric chloride, respectively. The Diels-Alder reaction of dimethoxy anthracene and benzenediazonium carboxylate in 1,2-dichloroethane yielded the dimethoxy triptycene derivative in 65% yield, which was then demethylated with BBr₃ to give the 2,7-dihydroxytriptycene in 89%. Reaction of 2,7-dihydroxytriptycene with cyanuric chloride in acetone in the presence of K₂CO₃ yielded two macrocycle isomers in 18% and 12%, respec­tively.