Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosa­tion of Amines, Amides and Ureas under Mild and Heterogeneous Conditions

Benoît Célariès; Cyril Párkányi

doi:10.1055/s-2006-942397

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Synthesis 2006(14): 2371-2375
DOI: 10.1055/s-2006-942397

PAPER

Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosation of Amines, Amides and Ureas under Mild and Heterogeneous Conditions

Benoît Célariès, Cyril Párkányi*
Department of Chemistry and Biochemistry, Florida Atlantic University, 777 Glades Road, P. O. Box 3091, Boca Raton, FL 33431-0991, USA
Fax: +1(561)2972759; e-Mail: parkanyi@fau.edu;

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Publication History

Received 1 February 2006
Publication Date:
15 May 2006 (online)

Abstract
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Abstract

We have developed a new method of N-nitrosation of various secondary and tertiary amines, amides and ureas using a mixture of tin(IV) chloride and sodium nitrate. This method leads to a selective, high-yielding and mild heterogeneous N-nitrosation by in situ generation of nitrosyl chloride (NOCl). The reaction can be carried out in several different solvents such as chloroform, dichloromethane, ethers, ethyl acetate and alcohols, at room temperature.

Key words

tin(IV) chloride - N-nitrosation - nitrosamines - nitrosoureas - nitrosamides

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