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Synthesis 2010(17): 2922-2925  
DOI: 10.1055/s-0030-1258192
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© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Synthesis of N-Cyano-Substituted Sulfilimines and Sulfoximines

Ankur Pandey, Carsten Bolm*
Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092391; e-Mail: Carsten.Bolm@rwth-aachen.de;
Further Information

Publication History

Received 8 July 2010
Publication Date:
04 August 2010 (online)

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Abstract

Starting from the corresponding sulfides, N-cyano sulfoximines can easily be accessed under metal-free conditions via the corresponding N-cyano-substituted sulfilimines. The reaction sequence involves a sulfide imination with cyanogen amide in presence of a base and N-bromosuccinimide (NBS) followed by an m-chloroperoxybenzoic acid (MCPBA) mediated oxidation of the resulting sulfilimine intermediates.

Key words

halides - metal-free - nitriles - sulfides - sulfilimines - sulfoximines

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9

Using I2 instead of NBS under those conditions led to the desired products in lower yields.

10

Attempting to use other oxidants such as KMnO4 for the sulfilimine oxidations led to lower sulfoximine yields.