The chemistry of polycyclic arene imines. I. Substitution at the nitrogen atom of 1a,9b‐dihydro‐1H‐phenanthro[9,10‐b]azirine

Chlorides of carboxylic, sulfonic and phosphoric acids proved to convert phenanthrene‐9,10‐imine into the corresponding rearranged acet‐ sulfon‐ and phosphonamidophenanthrene. Trimethylchlorosilane and N,O‐bis(trimethylsilyl)acetamide reacted with the imine without destruction of the aziridine ring. The silylated compound could be transferred into the respective N‐substituted phenanthrene‐9,10‐imines when treated with acetyl‐, methanesulfonyl‐, 4‐tosyl‐ and diethylphosphoryl chloride. A remarkably stable N‐chlorophenanthrene‐9,10‐imine was obtained from the unsubstituted compound and N‐chlorosuccinimide.