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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

S Shtelzer, T Sheradsky, J Blum…

文献索引:Shtelzer, Sarah; Sheradsky, Tuvia; Blum, Jochanan; Zitrin, Shmuel Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1593 - 1595

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被引用次数: 3

摘要

Abstract Methanolic silver nitrate and perchlorate convert N-chlorophenanthrene 9, 10-imine (1) into 10, 10-dimethoxy-9 (10H)-phenanthrone (2) in 60% yield. Substitution of the mthanol 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 ...