Russian Journal of Organic Chemistry

, Volume 47, Issue 12, pp 1789–1791 | Cite as

Acyl iodides in organic synthesis. Reaction of acetyl iodide with thiols

  • M. G. Voronkov
  • O. Yu. Grigor’eva
  • N. N. Vlasova


The direction of reactions of acetyl iodide with aliphatic, aromatic, and heterocyclic thiols is determined by the thiol acidity and steric factors. Acetyl iodide reacted with aliphatic thiols, including trialkylsilylsubstituted derivatives R(CH2) n SH (R = Me, n = 3; R = Me3Si, n = 3; R = Et3Si, n = 2), to give the corresponding ethanethioates R(CH2) n SCOMe. Benzenethiol was oxidized with acetyl iodide to diphenyl disulfide. The reaction of acetyl iodide with 2-sulfanylethanol afforded 2-(2-iodoethyldisulfanyl)ethyl acetate as a result of three consecutive-parallel processes: acylation, iodination, and oxidation of the initial compound. 1,3-Benzothiazole-2-thiol reacted with acetyl iodide only at the nitrogen atom to give quaternary salt, whereas the SH group remained intact.


Ethanethiol Benzenethiol PhSH Acetyl Iodide Diphenyl Disulfide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • M. G. Voronkov
    • 1
  • O. Yu. Grigor’eva
    • 1
  • N. N. Vlasova
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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