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Some reactions of 4,4-dichloro-3-buten-2-one

Communication 2. Reactions with sodium phenoxide and sodium phenyl sulfide

Summary

  1. 1.

    The reaction of 4,4-dichloro-3-buten-2-one with sodium phenoxide and with sodium phenyl sulfide was studied. The course of the reaction depends on the basic character of the medium and on the order in which the reactants are added.

  2. 2.

    The replacement of one of the chlorine atoms of 4,4-dichloro-3-buten-2-one by the phenylthio or phenoxy group occurs preferentially in the cis position with respect to the acetyl group.

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Literature cited

  1. 1.

    A. N. Nesmeyanov, O. A. Reutov, and A. S. Gudkova, Izv. AN SSSR. Otd. khim. n. 261 (1961).

  2. 2.

    A. N. Nesmeyanov and A. E. Borisov, Tetrahedron1, 138–168 (1954).

  3. 3.

    F. Montanari et al., Gazz. chim. ital.86, 735, 747 (1956);87, 1068, 1061, 1073 (1957).

  4. 4.

    G. Modena, Ricerca scient.28, 341 (1958).

  5. 5.

    W. Truce et al., J. Amer. Chem. Soc.80, 1916, 6450 (1958).

  6. 6.

    N. Kochetkov, B. P. Gottikh, V. G. Vinokurov, and R. M. Khomutov, Dokl. AN SSSR125, 89–92 (1959).

  7. 7.

    H. Shine and G. Hunt, J. Amer. Chem. Soc.80, 2434 (1958); N.Jang, R. Finnegan, J. Amer. Chem. Soc.80, 5845 (1958).

  8. 8.

    L. Crombil, Quart. Revs. London Chem. Soc.6, 137 (1952); S. Winstein, J. Amer. Chem. Soc.77, 3741 (1955); F. Montanari, Gazz. chim. ital.87, 1102 (1957).

  9. 9.

    N. K. Kochetkov and V. N. Vinogradova, Zh. obshch. khimii27, 2745 (1957).

  10. 10.

    H. Recher, Ber.48, 525 (1915).

  11. 11.

    H. Brintzinger and J. Janecke, Ber.83, 103 (1950).

  12. 12.

    H. Nordt, U. S. Pat.2729652 (1956); Chem. Abstrs.50, 13097f (1956).

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Additional information

For Communication 1, see [1].

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Gudkova, A.S. Some reactions of 4,4-dichloro-3-buten-2-one. Russ Chem Bull 11, 1172–1177 (1962). https://doi.org/10.1007/BF00908394

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Keywords

  • Sodium
  • Sulfide
  • Phenyl
  • Chlorine
  • Acetyl