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

Supporting Info

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

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

Org. Lett., 2002, 4 (3), pp 343–345

DOI: 10.1021/ol016979q

Publication Date (Web): January 5, 2002

†

IICT Communication No. 01/X/13.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sabitha@iict.ap.nic.in

Abstract

A convenient and efficient synthesis of 1,2-azidoalcohols and 1,2-azidoamines has been achieved by ring opening of epoxides and aziridines using cerium(III) chloride and sodium azide in acetonitrile. The reaction is highly regioselective and afforded the corresponding products in good to excellent yields under mild and neutral reaction conditions. The method is very rapid and equally compatible for both epoxides and aziridines.

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History

Published In Issue February 07, 2002
Received October 31, 2001
Revised December 20, 2001

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Letter

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