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

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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Details

The document discusses a novel, efficient, and regioselective method for the ring opening of epoxides and aziridines using sodium azide (NaN₃) and Oxone® in aqueous acetonitrile. This method converts epoxides and aziridines into corresponding β-azido alcohols and β-azido amines, respectively, under mild conditions at room temperature. The reactions are highly regioselective, yielding products with excellent yields and minimal side reactions. The use of Oxone® (potassium peroxymonosulfate) as a promoter is highlighted for its effectiveness, safety, and cost-efficiency. The study demonstrates that 0.5 equivalents of Oxone® are necessary for complete conversion, and reducing this amount results in lower yields and incomplete reactions. The method is applicable to various substrates, including those with oxidation-sensitive functionalities, without producing side products. The document provides detailed experimental procedures and characterizations of the products obtained. The advantages of this protocol include operational simplicity, high regioselectivity, short reaction times, and the ability to handle both epoxides and aziridines efficiently. This method is expected to be valuable in synthetic organic chemistry for the preparation of azido alcohols and amines, which are important intermediates in pharmaceuticals and natural products.

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