Organic Chemistry Portal



Ring Opening of Epoxides and Aziridines with Sodium Azide using OxoneŽ in Aqueous Acetonitrile: A Highly Regioselective Azidolysis Reaction

Gowravaram Sabitha*, R. Satheesh Babu, M. Shashi Kumar Reddy, J. S. Yadav

*Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email:

G. Sabitha, S. R. Babu, M. S. K. Reddy, J. S. Yadav, Synthesis, 2002, 2254-2258.

DOI: 10.1055/s-2002-34848


A wide variety of epoxides and aziridines were converted to the corresponding β-azido alcohols and β-azido amines with sodium azide using OxoneŽ in aqueous acetonitrile. The reactions were highly regioselective and efficient with excellent yields at room temperature under mild reaction conditions.

see article for more examples

Cerium(III) Chloride Promoted Highly Regioselective Ring Opening of Epoxides and Aziridines Using NaN3 in Acetonitrile: A Facile Synthesis of 1,3-Azidoalcohols and 1,2-Azidoamines

G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Vadav, Org. Lett., 2002, 4, 343-345.

Key Words

Oxone, epoxides, aziridines, azides (1,2-azidoalcohols, 1,2-azidoamines), regioselectivity

ID: J66-Y2002-1650