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

Gowravaram Sabitha*, R. Satheesh Babu, M. Rajkumar and J. S. Vadav

*Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: sabithaiict.ap.nic.in

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

DOI: 10.1021/ol016979q

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Abstract

A convenient, efficient, and highly regioselective synthesis of 1,2-azidoalcohols and 1,2-azidoamines in excellent yields has been achieved by using cerium(III) chloride and sodium azide for a mild ring opening of epoxides and aziridines.

see article for more examples

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

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

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Key Words

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

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ID: J54-Y2002-720