79699-55-1Relevant 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
Synthesis of 1,1-dimethyl-4-indanol derivatives
Wang, Yang,Wu, Jiang,Xia, Peng
, p. 2685 - 2698 (2007/10/03)
The synthesis of 1,1-dimethyl-4-indanols (3a,b) has been achieved by intramolecular Friedel-Crafts cyclization of 2-(3-methyl-2-butenyl)phenols (5a,b) or 1-methoxy-2-(3-methyl-2-butenyl)benzenes (6a,b) followed by demethylation, respectively. It was found that the solvent was critical for the formation of different products in the intramolecular Friedel-Crafts reactions of 6. The unexpected product 4-methoxy-1,1,6,6-tetramethyl-as-hydrindacene (11) was obtained from the Friedel-Crafts reactions of 6a and its structure was confirmed by X-ray diffraction analysis. The key intermediates 5a,b were prepared by ortho-alkenylation of phenols with 1-bromo-3-methyl-2-butene, and the reaction temperature exerted an obvious impact on the yield of 2-(3-methyl-2-butenyl)phenol (5a). Copyright Taylor & Francis Group, LLC.
