Studies of Acenaphthene Derivatives. XII. On the Red Substance Obtained from Acenaphthenequinone and Ammonia

Abstract

Abstract In order to elucidate the chemical structure of red crystals (A) obtained from the reaction of acenaphthenequinone (I) with ammonia, the reaction of I with ammonia, formamide or benzylamine was reinvestigated. It has been made clear again that the compound A is not acenaphthazine (II) but acenaphtho[l, 2-b]isoimidazole-2-spiro-2′-acenaphthenone (III), and that Schonberg’s assumption of the structure of the compound A is incorrect. That reaction of I with benzylamine afforded II as yellow needles in a good yield. Also, it has been found that the reaction product (B) of I with formamide is a mixture of almost equal amounts of II and III.