Nitration of Polycyclic Aromatic Hydrocarbons with Nitryl Chloride

Abstract

The nitration of acenaphtylene, phenanthrene and anthracene by means of nitryl chloride as a nitrating agent has been studied. These reaction were carried out in carbon tetrachloride at temperatures between -5 and +5°C without using catalyst or light. In the cases of acenaphtylene and phenanthrene, the nitration reaction took place selectively and gave 1-nitroacenaphtylene [1] and 9-nitrophenanthrene[2] respectively. On the other hand, 9-chloro-10- nitro-9, 10-dihydroanthracene [5] was obtained from anthracene along with 9-nitroanthracene [6]. It is noted that nitryl chloride is a selective nitrating agent for acenaphtylene and phenanthrene and superior to the other nitrating agents for this purpose.