Kinetics and Mechanism of the Aminolysis of Aryl N-Cyclohexyl Thiocarbamates in Acetonitrile

A simple and efficient process for direct generation of various S-thiocarbamates is developed by cross-coupling of readily available sulfonyl chlorides with cyclohexyl isocyanide. The yields are excellent and the structures of the generated S-thiocarbamates are characterized by nuclear magnetic resonance spectroscopy, infrared spectroscopy, and high-resolution mass spectrometry together with X-ray crystallographic analysis. The protocol has the advantages of using easily available reagents, employs inexpensive KI as the reagent, demonstrates good functional group tolerance, and utilizes mild reaction conditions.

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Kinetics and Mechanism of the Aminolysis of Thiophenyl Cyclohexanecarboxylates

Hong²

2009

Bulletin of the Korean Chemical Society

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Kinetics and Mechanism of the Aminolysis of Aryl N-Cyclohexyl Thiocarbamates in Acetonitrile

Cited by 12 publications

References 28 publications

Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

KI-catalyzed synthesis of S-Thiocarbamates by cross-coupling of cyclohexyl isocyanide with sulfonyl chlorides

Kinetics and Mechanism of the Aminolysis of Thiophenyl Cyclohexanecarboxylates

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