Cyclization of deprotonated 2-phenyl-1-tosylaziridine. A surprising example of an intramolecular nucleophilic aromatic addition

Article abstract of DOI:10.1016/S0040-4039(00)79650-X

Deprotonation of 2-phenyl-1-tosylaziridine 1 with butyl lithium gives an anion that cyclizes to 4 by an intramolecular nucleophilic aromatic addition. Treatment of derivatives 5, 6 with a Gringnard reagent produces aziridines 10, 11.