REACTIONS OF CUPRIC HALIDES WITH ORGANIC COMPOUNDS .V. REACTIONS OF 9,10-DIALKYL- AND 9-ALKYL-10-ARYLANTHRACENES

9-Aryl-10-methylanthracenes undergo reaction with cupric halides to give the corresponding 9-aryl-10-halogenomethylanthracenes. 9-Ethyl- and 9-benzyl-10-methylanthracenes similarly undergo reaction at the Me group rather than at the Et or Bz groups to form the halogenomethyl compound. These results indicate that the 9-alkyl-10-anthrylmethyl radical is more stable than the radicals which would be formed by hydrogen abstraction from the Et or Bz groups. These reactions also gave products in which alkyl groups were replaced by halogen. A mechanistic interpretation of these results is advanced. The reactions of 9-alkyl (or aryl) 10-methylanthracenes with N-bromosuccinimide were also examined. © 1969.