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Synthesis of N-Sulfenylimines from Disulfides and Primary Methanamines

Robert Kawȩcki*

*Faculty of Sciences, Siedlce University, 3 Maja Street No. 54, Siedlce 08-110, Poland, Email:

R. Kawȩcki, J. Org. Chem., 2022, 87, 7514-7520.

DOI: 10.1021/acs.joc.2c00415

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N-Sulfenylimines were efficiently synthesized in good yields through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results.

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proposed mechanism

Key Words

N-Sulfenylimines (oxidation, coupling), NBS

ID: J42-Y2022