The chemistry of polycyclic arene imines. V. Reactions of phenanthrene 9, 10??imine with nucleophiles under phase transfer conditions

M Weitzberg, Z Aizenshtat…

Index: Weitzberg, Moshe; Aizenshtat, Zeev; Blum, Jochanan Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1597 - 1601

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Citation Number: 8

Abstract

Abstract Reactions of phenanthrene 9, 10-imine (1) with alkyl halides, sodium azide and ammonium thiocyanate in two liquid phase systems were investigated. In the presence of aqueous sodium hydroxide and alkyl halides triethylbenzylammonium (TEBA) salts promote N-alkylation of 1 with preservation of the aziridine ring. Tetrabutylammonium (TBA) salts catalyze nucleophilic substitutions in which the three membered ring is cleaved. Aqueous ...