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Thiocarbamate

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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

References

  1. ^ March, 6th edn., p. 1269
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