Russian Journal of Organic Chemistry

, Volume 39, Issue 12, pp 1702–1705 | Cite as

Acyl Iodides in Organic Synthesis: IV. Reaction of Acetyl Iodide with Carboxylic Acids

  • M. G. Voronkov
  • L. I. Belousova
  • A. A. Trukhina
  • N. N. Vlasova
Article

Abstract

In contrast to acyl chlorides, reactions of acetyl iodide with monocarboxylic acids follow the exchange pattern to give the corresponding acyl iodides and acetic acid. The reaction attracts interest from the preparative viewpoint as a simple and convenient route to acyl iodides. Acetyl iodide reacts with phthalic acid, yielding acetic acid and phthalic anhydride, while the reaction of acetyl iodide with oxalic acid leads to formation of acetic acid, carbon(II) oxide, and molecular iodine.

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REFERENCES

  1. 1.
    Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1576.Google Scholar
  2. 2.
    Voronkov, M.G. and Shagun, V.A., Russ. J. Org. Chem., 2003, vol. 39, p. 331.Google Scholar
  3. 3.
    Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1579.Google Scholar
  4. 4.
    Voronkov, M.G. and Khudobin, A.Yu., Izv. Akad. Nauk SSSR, Ser. Khim., 1956, p. 713.Google Scholar
  5. 5.
    Voronkov, M.G., Pavlov, S.F., Dubinskaya, E.I., and Puzanova, V.E., Abstracts of Papers, IV Mezhdunarodnyi simpozium po khimii kremniiorganicheskikh soedinenii (IVth Int. Symp. on the Chemistry of Organosilicon Compounds), Moscow, 1975, vol. 1, p. 184.Google Scholar
  6. 6.
    Voronkov, M.G., Puzanova, V.E., Pavlov, S.F., and Dubinskaya, E.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1975, p. 390.Google Scholar
  7. 7.
    Voronkov, M.G., Pavlov, S.F., and Dubinskaya, E.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1975, p. 657.Google Scholar
  8. 8.
    Voronkov, M.G., Dubinskaya, E.I., and Pavlov, S.F., Abstracts of Papers, VIIth Int. Conf. of Organometallic Chemistry, Venice, 1975, p. 155.Google Scholar
  9. 9.
    Voronkov, M.G. and Dubinskaya, E.I., J. Organomet. Chem., 1991, vol. 410, p. 1.Google Scholar
  10. 10.
    Voronkov, M.G., Vlasova, N.N., and Trukhina, A.A., Sovremennyi organicheskii sintez (Contemporary Organic Synthesis), Moscow-Ufa: Khimiya-Reaktiv, 2003, p. 9.Google Scholar
  11. 11.
    The Chemistry of Acyl Halides, Patai, S., Ed., London: Intersci., 1972, p. 177.Google Scholar
  12. 12.
    Edward, H., O'Neal, H.E., and Benson, S.W., J. Chem. Phys., 1962, vol. 37, p. 540.Google Scholar
  13. 13.
    O'Neal, H.E. and Benson, S.W., J. Chem. Phys., 1962, vol. 37, p. 540.Google Scholar
  14. 14.
    Haszeldine, R.N., J. Chem. Soc., 1951, p. 584.Google Scholar
  15. 15.
    Sonntag, N.O., Chem. Rev., 1953, vol. 52, p. 237.Google Scholar
  16. 16.
    Schmidt, A.H., Russ, M., and Grosse, D., Synthesis, 1981, no. 3, p. 216.Google Scholar
  17. 17.
    Hoffman, H.M. and Haase, K., Synthesis, 1981, no. 9, p. 715.Google Scholar
  18. 18.
    Gal, I., C. R. Acad. Sci., 1873, p. 1021.Google Scholar
  19. 19.
    Theobald, D.W. and Smith, J.C., Chem. Ind., 1958, p. 1007.Google Scholar
  20. 20.
    Spravochnik khimika (Chemist's Handbook), Nikol'skii, B.P., Ed., Moscow: Khimiya, 1963, vol. 2.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2003

Authors and Affiliations

  • M. G. Voronkov
    • 1
  • L. I. Belousova
    • 1
  • A. A. Trukhina
    • 1
  • N. N. Vlasova
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of SciencesIrkutskRussia

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