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Organosulfur compounds of the forms ROC(S)NR2 or RSC(O)NR2 From Wikipedia, the free encyclopedia
In organic chemistry, thiocarbamates (thiourethanes) are a family of organosulfur compounds. As the prefix thio- suggests, they are sulfur analogues of carbamates. There are two isomeric forms of thiocarbamates: O-thiocarbamates, ROC(=S)NR2 (esters), and S-thiocarbamates, RSC(=O)NR2 (thioesters).
Thiocarbamates can be synthesised by the reaction of water or alcohols upon thiocyanates (Riemschneider thiocarbamate synthesis):[1][2]
Similar reactions are seen between alcohols and thiocarbamoyl chlorides such as dimethylthiocarbamoyl chloride; as well as between thiols and cyanates.[2] The herbicide Cycloate is produced in this way:
Other related thiocarbamate herbicides include vernolate (C3H7)2NCOSC3H7 and triallate ((i−C3H7)2NCOSCH2CCl=CCl2.[3]
Salts of thiocarbamate arise by the reaction of amines with carbonyl sulfide:
In the Newman-Kwart rearrangement O-thiocarbamates can isomerise to S-thiocarbamates.[4] This reaction, which generally requires high temperatures, is an important method for the synthesis of thiophenols.
Goitrin is a cyclic thiocarbamate found in some vegetables.[5]
Thiocarbamate based herbicides (e.g. prosulfocarb) were introduced in 1957 and in 2017 was a $200,000,000 market.[6]
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