Abstract
Reduction of 9,10-dicyanoanthracene with one equivalent of metallic potassium in liquid ammonia at -33°C gives a product which almost does not react with butyl bromide. By contrast, the two-electron reduction product reacts with butyl bromide to form, depending on the reaction conditions and procedure for treatment of the reaction mixture, one of the three compounds: 10-butyl-9-cyanoanthracene, 10-butyl-10-cyano-9,10-dihydroanthracen-9-one, or 9,10-dibutyl-9,10-dicyano-9,10-dihydroanthracene. Relatively stable 10-butyl-9,10-dicyano-9,10-dihydro-9-anthryl anion was presumed to be a common precursor of these products.
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Vaganova, T.A., Pokrovskii, L.M. & Shteingarts, V.D. Reductive Activation of Arenes: XIII. Reaction with Butyl Bromide of Anionic Products Formed by Reduction of 9,10-Dicyanoanthracene with Potassium in Liquid Ammonia. Russian Journal of Organic Chemistry 37, 62–66 (2001). https://doi.org/10.1023/A:1012373300561
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DOI: https://doi.org/10.1023/A:1012373300561