40650-33-7Relevant academic research and scientific papers
Facile preparation and molecular structure of a novel metacyclophane
Zhang, Jing-Lei,Shi, Qi,Wu, Jiang,Wang, Yang
, p. 2341 - 2348 (2008/09/21)
A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel-Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at - 78°C using TiCl4 as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl[3.3.3]metacyclophane derivative. Demethylation of 2 with BBr3 gave 1,1,10,10,19,19-hexamethyl-5,14, 23-trihydroxy[3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies. Copyright Taylor & Francis Group, LLC.
