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Acylation of arsenic β-ketoylides by carboxylic acid halides

  • N. A. Nesmeyanov
  • V. G. Kharitonov
  • S. T. Berman
  • P. V. Petrovskii
  • O. A. Reutov
Organic Chemistry
  • 23 Downloads

Conclusions

  1. 1.

    In contrast to the corresponding phosphorus ylide, triphenylarsinebenzoylmethylene is acylated by acyl bromides at two reaction centers: at the O and C atoms. Triphenylarsineacetylmethylene gives only an O-acylation product.

     
  2. 2.

    In contrast to the phosphorus analogs, acyloxyvinylarsonium salts rearrange on heating into the C-acylated analogs.

     
  3. 3.

    During rearrangement of β-substituted benzoyloxyvinyltriphenylarsoriium bromides in the presence of sodium acetate and β-substituted acetoxyvinyltriphenylarsonium bromides in the presence of sodium benzoate, one and the same mixture of diacyl ylides is formed. It was shown that the rearrangement proceeds via the stage of splitting of the acyl group, followed by C-acylation of the ylide formed by an anhydride.

     

Keywords

Sodium Acetate Phosphorus Bromide Arsenic 
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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Literature cited

  1. 1.
    P. A. Chopard, J. G. Searle, and P. H. Devitt, J. Org. Chem.,30, 1015 (1965).Google Scholar
  2. 2.
    N. A. Nesmeyanov, S. T. Berman, O. A. Rebrova, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 192 (1982).Google Scholar
  3. 3.
    N. A. Nesmeyanov, S. T. Berman, P. V. Petrovskii, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 2805 (1980).Google Scholar
  4. 4.
    N. A. Nesmeyanov, V. G. Kharitonov, S. T. Berman, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 700 (1983).Google Scholar
  5. 5.
    A. W. Johnson and H. Schubert, J. Org. Chem.,35, 2678 (1970).Google Scholar
  6. 6.
    N. A. Nesmeyanov, V. G. Kharitonov, S. T. Berman, P. V. Petrovskii, and O. A. Reutov, Dokl. Akad. Nauk SSSR,274, 606 (1984).Google Scholar
  7. 7.
    I. Goshey and D. Lloyd, Tetrahedron,29, 1697 (1973).Google Scholar
  8. 8.
    F. Krohnke, Chem. Ber.,83, 291 (1951).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • N. A. Nesmeyanov
    • 1
  • V. G. Kharitonov
    • 1
  • S. T. Berman
    • 1
  • P. V. Petrovskii
    • 1
  • O. A. Reutov
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR

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