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.[1]

Synthesis[edit]

Thiocarbamates can be synthesised by hydrolysis of thiocyanates:[2]

RSCN + H2O → RSC(=O)NH2

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

Alternatively, they arise by the reaction of amines with carbonyl sulfide:

2 R2NH + COS → [R2NH2]+][R2NCOS]

Dithiocarbamates[edit]

The general structure of a dithiocarbamate ester.

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.[3]

See also[edit]

References[edit]

  1. ^ Melvin S. Newman, Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139. 
  2. ^ March, 6th edn., p. 1269
  3. ^ 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