Reactions with aziridines, 53. — Arene hydrides, 9. intermediate substitution in the formation of a benzylic anion by an aromatic radical anion as observed with 1‐benzoyl‐2‐phenylaziridine

The reaction of the title compound 1 with anthracene hydride AH‐ or anthracenide A‐' leads to the formation of the ben‐ zylic anion 9 by fragmentation of the first generated substi‐ tution intermediate 7 or 8. In the reactions with AH‐ the carb‐ anion 9 is completely trapped by protonation with dihydroan‐ thracene AH2 yielding the reduction product 3 (N‐benzoyl‐phenethylamine).phenethylamine). In reactions with A‐' as well as with naph‐ thalenide N‐' the carbanion 9 either abstracts a proton from the solvent THF (yielding 3) or adds to the benzoyl group of unreacted 1 which finally results in P‐benzamido‐ct‐phenyl‐ propiophenone (6).