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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
Author(s) -
Shtelzer Sarah,
Sheradsky Tuvia,
Blum Jochanan,
Zitrin Shmuel
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210605
Subject(s) - chemistry , imine , yield (engineering) , medicinal chemistry , methanol , silver nitrate , nucleophile , ethanol , perchlorate , nucleophilic substitution , organic chemistry , nucleophilic addition , ion , catalysis , materials science , metallurgy
Methanolic silver nitrate and perchlorate convert N ‐chlorophenanthrene 9,10‐imine (1) into 10,10‐dimethoxy‐9(10 H )‐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 a cyclic nitrenium ion, nucleophilic ring opening by methanol, hydrolysis of the imine function and silver ion promoted oxidation.