Thiocarbamate

General structural formulae of O-organyl (1) and S-organyl (2) thiocarbamates

Thiocarbamates are a family of organosulfur compounds. There are two isomeric forms of thiocarbamate esters: O-thiocarbamates, ROC(=S)NR₂, and S-thiocarbamates, RSC(=O)NR₂. O-thiocarbamates can isomerise to S-thiocarbamates, for example in the Newman-Kwart rearrangement.

Synthesis

Thiocarbamates can be synthesised by hydrolysis of thiocyanates:^[1]

RSCN + H₂O → RSC(=O)NH₂

Where R is aryl, this method is known as the Riemschneider thiocarbamate synthesis.

See also

• Tolnaftate
• Goitrin
• Carbamate
• Dithiocarbamate

References