REACTION OF 9-NITROANTHRACENE WITH SODIUM CYANIDE IN DIMETHYLFORMAMIDE

The interaction of 9-nitroanthracene with sodium cyanide in DMF at room temperature gives a solution which exhibits an electron paramagnetic resonance signal and from which a series of products, including 9-cyano-10-nitroanthracene, 9-amino-10-cyanoanthracene, 9,10-dicyanoanthracene, 9-cyano-10-anthranol, and 9-cyano-10-anthrone can be isolated. Product distributions under a variety of reaction conditions have been studied. Product formation is discussed in terms of oxidation-reduction of a Meisenheimer adduct and nucleophilic substitution. © 1968, American Chemical Society. All rights reserved.