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Arylmercury derivatives of ketoenols and phenols

  • A. N. Nesmeyanov
  • D. N. Kravtsov
Organic and Biological Chemistry

Summary

  1. 1.

    In the ketoenofic tautomeric system of β-dicarbonyl compounds, the arylmercury radical forms only C-derivatives (which readily undergo symmetrization in the majority of cases), being in this respect similar to the atom of mercury and differing markedly from hydrogen, for which two types of compounds are characteristic — the enof and the ketone- and other metals, derivatives of which have a purely enofate structure.

     
  2. 2.
    The arylmercury derivatives of phenofs obtained under mild conditions are O-derivatives, no isomerization of which into the keto-form with subsequent formation of an arylmercurated phenof takes place
    $$\begin{array}{*{20}c} \hfill {OHgR} \\ \hfill | \\ \hfill { / \setminus \setminus } \\ \hfill {|||} \\ \hfill { \setminus / / } \\ \end{array} \mathop { - \to }\limits^{||} \begin{array}{*{20}c} \hfill O \\ \hfill {||} \\ \hfill { / \setminus } \\ \hfill {||||} \\ \hfill { \setminus / } \\ \hfill | \\ \hfill {HgR} \\ \end{array} \to \begin{array}{*{20}c} \hfill {OH} \\ \hfill | \\ \hfill { / \setminus \setminus } \\ \hfill {|||} \\ \hfill { \setminus / / } \\ \hfill | \\ \hfill {HgR} \\ \end{array}$$
    In this respect, the arylmercury radical differs from mercury, the phenoxides of which are unstable and are readily isomerized into mercurated phenofs.
     
  3. 3.

    In respect of its behavior in a ketoenofic tautomeric system, an arylmercury radical occupies an intermediate position between mercury and a hydrogen atom; for the ketoenof derivatives, as for mercury, the keto form is stable; for the phenof derivatives, as for hydrogen, the enofate structure is stable.

     

Keywords

Hydrogen Phenol Mercury Hydrogen Atom Ketone 
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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Copyright information

© Consultants Bureau 1963

Authors and Affiliations

  • A. N. Nesmeyanov
    • 1
  • D. N. Kravtsov
    • 1
  1. 1.Institute of Heteroorganic Compounds of the Academy of Sciences of the USSRUSSR

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