Alkyl and aryl isothiocyanates as masked primary amines

Primary and secondary (but not tertiary) alkyl as well as aryl isothiocyanates react rapidly with 4-methyl1-1,2benzenedithiol (1) in methanol at room temperature, releasing the corresponding amines in good yields. This mild and simple procedure for unmasking amines proceeds chemospecifically with isothiocyanates even in the presence of such normally electrophyllic and reactive functionalities as carbolyxate ester and N-alkylphalimide.