[uglepik]

In our lab we are currently playing around with isothiocyanates. They are usually seen to react with nitrogen nucleophiles (amines) to form thioureas. We have been wondering whether the isothiocyante (-N=C=S) can also react with oxygen species such as water/hydroxide or alcohols/alcoxides. The product would be a thiocarbamate.

Does anyone know or have any experience with this?

[Hunter2]

Yes they will do. You will get Thio urethanes if you react with alcohols. At least the same compounds like Iso cyanates form with other nucleophiles. Amines will get Thiourea. Water will form Thiocarbamate.