Chlorination by Hypochlorous Acid. Free-Radical Versus Electrophilic Reactions

  • F. Fontana
  • F. Minisci
  • E. Vismara
  • G. Faraci
  • E. Platone
Part of the NATO ASI Series book series (ASIC, volume 260)

Abstract

The chlorination at room temperature of alkanes, aromatics, alkylaromatics, olefins with hypochlorous acid shows two competitive processes in the absence of freeradical initiators: a free-radical chain chlorinatinn and an electrophilic process, whenever this last is structurally possible. The factors affecting this competition, the mechanism of the free-radical chain involved, the selectivity and the synthetic potentiality of this new procedure of free-radical chlorination are discussed.

Keywords

Chlorine Atom Radical Chain Hypochlorous Acid Benzyl Chloride Electrophilic Substitution 
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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References

  1. 1.
    “Aromatic Substitution. Nitration and Halogenation”. P.B.D. De La Mare, J.H. Ridd, Butterwords, London 1959, pag.16.Google Scholar
  2. “Electrophilic Substitutions in Benzenoid Compounds”, R.O.C. Norman, R. Taylor, Elsevier, London, 1965, pag.119.Google Scholar
  3. 2.
    M.L. Poutsma, Methods in Free-Radical Chemistry, vol.1, 79, 1969.Google Scholar
  4. 3.
    C. Walling, B.B. Jacknow, J.Am.Chem.Soc. 1960, 82, 6108, 6113.CrossRefGoogle Scholar
  5. 4.
    F. Minisci, E. Platone, G. Serboli, U.S.P. 4.423.263 (15/7/1980).Google Scholar
  6. 5.
    F.D. Marsh, W.B. Fornham, D.J. Sam, B.E. Smart, J.Am.Chem.Soc. 1982, 104, 4680.CrossRefGoogle Scholar
  7. 6.
    G.A. Russell, J.Am.Chem.Soc., 1958, 80, 4987.CrossRefGoogle Scholar
  8. 7.
    G.A. Russell and H.C. Brown, J.Am.Chem.Soc. 1955, 77, 4578.CrossRefGoogle Scholar
  9. 8.
    G. Faraci, E. Platone, F. Minisci, Ital.Pat. 1.161.227 (1983).Google Scholar
  10. 9.
    H.E. Fanouni, S. Krishnan, D.G. Kuhn, G.A. Hamilton, J.Am.Chem.Soc. 1983, 105, 7672.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • F. Fontana
    • 1
  • F. Minisci
    • 1
  • E. Vismara
    • 1
  • G. Faraci
    • 2
  • E. Platone
    • 2
  1. 1.Dipartimento di Chimica del PolitecnicoMilanoItaly
  2. 2.EniricercheS. Donato Milanese, MilanoItaly

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