Ring Opening of Epoxides and Aziridines with Sodium Azide using Oxone® 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: sabithaiictnet.org

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

DOI: 10.1055/s-2002-34848

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Abstract

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

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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.

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Key Words

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

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ID: J66-Y2002-1650