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
Article

Abstract

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.

Keywords

Ethanethiol Benzenethiol PhSH Acetyl Iodide Diphenyl Disulfide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1576.CrossRefGoogle Scholar
  2. 2.
    Jung, M.E. and Ornstein, P.L., Tetrahedron Lett., 1977, vol. 31, p. 2659.CrossRefGoogle Scholar
  3. 3.
    Sonntag, N.O.V., Chem. Rev., 1953, vol. 52, p. 237.CrossRefGoogle Scholar
  4. 4.
    Kivineu, A., The Chemistry of Acyl Halides, Patai, S., Ed., London: Interscience, 1972, p. 177.CrossRefGoogle Scholar
  5. 5.
    Organic Chemistry of Sulfur, Oae, S., Ed., New York: Plenum, 1977.Google Scholar
  6. 6.
    The Chemistry of the Thiol Group, Patai, S., Ed., London: Wiley, 1974, vol. 2, p. 785.Google Scholar
  7. 7.
    Voronkov, M.G., Vlasova, N.N., Grigor’eva, O.Yu., Belousova, L.I., and Vlasov, A.V., Russ. J. Org. Chem., 2009, vol. 45, p. 486.CrossRefGoogle Scholar
  8. 8.
    Voronkov, M.G., Vlasova, N.N., Adamovich, M.Yu., Pozhidaev, Yu.N., and Kirillov, A.I., Zh. Obshch. Khim., 1984, vol. 54, p. 865.Google Scholar
  9. 9.
    Mironov, V.F. and Pogonkina, N.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, p. 85.Google Scholar
  10. 10.
    Aivazov, B.V., Petrov, S.M., Khairullina, V.R., and Yapryntseva, V.G., Fiziko-khimicheskie konstanty sero-organicheskikh soedinenii (Physicochemical Constants of Organosulfur Compounds), Moscow: Khimiya, 1964.Google Scholar

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

Personalised recommendations