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

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
Copyright © 2002 American Chemical Society

 IICT Communication No. 01/X/13.

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*

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

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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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