Friedel–Crafts acylations of aromatic hydrocarbons. Part X. Benzoylation of phenanthrene

Abstract

Friedel–Crafts benzoylation of phenanthrene afforded mixtures of the five isomeric benzoylphenanthrenes. In chloroalkane or carbon disulphide solvents the yields of isomers were in the order: 9- > 3- > 1- > 2- > 4-; in nitromethane and nitrobenzene the yields of the 3- and 2-isomers were increased at the expense of those of the 9- and 1-isomers. Relative reactivities measured for competitive benzoylations in chloroform solution were: 9-phenanthryl 2·69, 3-phenanthryl 2·60, 1-phenanthryl 1·72, 1-naphthyl 1·00, 2-phenanthryl 0·64, 2-naphthyl 0·40, and 4-phenanthryl 0·26.