| Abstract: | Reaction of anthracenide A ·‐ with N‐benzoylaziridines 1a,b forms charged radicals 3a,b by single electron transfer and homolytic ring opening. Reactions follow that are known or expected as e.g. coupling with position 9 of A ·‐ forming dihydroanthracene anions 9a,b that yield amidoethylated dihydroanthracenes 10a,b , or react with 1a,b giving finally 9,10‐bis‐amidoethylated dihydroanthracenes 11a,b . Results depend on experimental conditions and on the counter ions Na+ or Li+. Coupling is not regiospecific: contributions by positions 2 and 1 reach 29% or 4%, respectively, of total coupling with the primary radical 3a ; much higher contributions are possible with Li. Product 21s (probably 3,3′‐disubstituted tetrahydrobianthryl) may arise by hydrogen detachment from the first intermediate ( 29 ) of coupling with position 2 and dimerization of the formed 2‐substituted A ·‐ ( 30 ). Coupling products may be fully aromatized or may be hydroxylated in one of the benzylic positions. With counter ion Li+ a non‐SET reaction of 1a with the dimer of A ·‐ is indicated by the isolation of 9‐benzoyl‐dihydroanthracene 15 and by 19% yield of 16a (aromatized 10a ). Reaction of 3b with anthracene is indicated by 10,10′‐disubstituted tetrahydrobianthryl 37 . |
