27111-62-2Relevant academic research and scientific papers
Reactions of Copper(II) Halides with Aromatic Compounds. Part XIII. The Mechanism of Halogenation of some Substituted 9-methylanthracenes.
Alcorn, William C.,Cromarty, Fiona M.,Flood, James,Mancilla, Jerson,Mosnaim, A. David,et al.
, p. 1620 - 1642 (2007/10/02)
Halogenations of 2-chloro-9-methylanthracene and 2,9-dimethylanthracene with copper(II) bromide in refluxing carbon tetrachloride and copper(II) chloride in refluxing chlorobenzene give exclusively the corresponding 10-halogenated products whereas brominations under radical conditions give the 9-bromoethyl compounds.These results support a mechanism involving direct attack by the copper(II) halide on the substrate, probably via a ?-complex between the copper(II) halide and the substituted anthracene, to give initially a 10-halogeno-9-methyl-9,10-dihydro-9-anthryl radical.Halogenation of 1,4,9-trimethylanthracene with copper(II) halides, a much slower reaction, is postulated to proceed by an electron-transfer mechanism.
