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The Chemistry of Arene Imines. IV. An Unusual Silver Promoted Transformation of N-Chlorophenanthrene 9,10-Imine into 9,10-Phenanthrenequinone Dialkyl Acetals
Shtelzer, Sarah,Sheradsky, Tuvia,Blum, Jochanan,Zitrin, Shmuel
, p. 1593 - 1595 (2007/10/02)
Methanolic silver nitrate and perchlorate convert N-chlorophenanthrene 9,10-imine (1) into 10,10-dimethoxy-9(10H)-phenanthrone (2) in 60percent yield.Substitution of the methanol by ethanol, 1- and 2-propanol gives phenanthrenequinone diethyl-, di-1-propyl- and di-2-propylacetals (3-5), respectively.Silver acetate promotes these transformations only in the presence of a protic acid.The reaction mechanism is assumed to involve the generation of a cyclic nitrenium ion, nucleophilic ring opening by methanol, hydrolysis of the imine function and silver ion promoted oxidation.
