Sc. Bergmeier et Dm. Stanchina, A DIRECTED AMIDOHALOGENATION REACTION - AN UNUSUAL REACTION OF AZIDOFORMATES, Tetrahedron letters, 36(26), 1995, pp. 4533-4536
The thermal intramolecular reaction of an azidoformate and an olefin d
oes not provide the expected aziridine, but rather an amidohalide. Thi
s unusual product is formed via an intramolecular nitrene addition to
the olefin to initially provide an aziridine. Under the reaction condi
tions HCl is generated from the solvent which protonates and opens the
aziridine providing the observed product. This reaction proceeds with
good stereoselectivity giving stereoisomeric ratios of 3:1 to 6.7:1.