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

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.

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

References

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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.