16204-72-1Relevant academic research and scientific papers
Selective sp3 C-H bond activation based on a carbocation relay: Friedel-Crafts reaction with alkanes as the alkylating component
Wang, Jie,Zhou, Pengfei,Wang, Yang
experimental part, p. 264 - 270 (2011/03/20)
A highly efficient and selective intramolecular Friedel-Crafts reaction of 3-methylbutyl or 4-methylpentyl-substituted aromatics has been developed using a carbocation relay strategy through selective sp3 C-H bond activation, providing a facile and cost-effective approach for the construction of benzocyclic compounds. A variety of 1,1-dimethylindane and naphthalene derivatives have been prepared from very simple starting materials in good yields with high selectivity. The present strategy has provided a new example of a Friedel-Crafts reaction with alkanes as the alkylating component and constitutes a convenient approach to selective C-H bond activation and functionalization of alkane derivatives. A highly efficient and selective intramolecular Friedel-Crafts reaction of 3-methylbutyl or 4-methylpentyl- substituted aromatics has been developed using a carbocation relay strategy through selective sp3 C-H bond activation. The approach provides a facile and cost-effective route to benzocyclic compounds. Copyright
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.
