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Gdańsk University of Technology

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A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides.

We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.

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