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.
- RSCN + H2O → RSC(=O)NH2
Alternatively, they arise by the reaction of amines with carbonyl sulfide:
- 2 R2NH + COS → [R2NH2]+][R2NCOS]−
Dithiocarbamates are related to thiocarbamates by the replacement of O by S. Despite this structural similarity their synthesis and chemistry is quite different. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.
- Melvin S. Newman, Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.
- March, 6th edn., p. 1269
- Engels, Hans-Wilhelm; et al. (2005), "Rubber, 4. Chemicals and Additives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a23_365.pub2
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