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Optically active organomercury compounds Communication 2. Mechanism of electrophilic substitution at a saturated carbon atom

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Two diastereoisomers of the di-(-)-menthyl ester of mercuribis[phenylacetic acid] have been prepared in the pure state.

  2. 2.

    The mechanism of the symmetrization of organomercury compounds of the aliphatic series under the action of nucleophilic reagents has been elucidated.

  3. 3.

    The stereochemical course of an electrophilic-substitution reaction at a saturated carbon atom has been investigated for the first time, the examples studied being the symmetrization of diastereoisomeric menthyl esters of (bromomercuri)phenyl-acetic acid and the reaction of the diasteaeoisometic di-(-)-menthyl esters of mercuribis[phenyl acetic acid] with mercuric bromide. It has been shown, that the electrophilic-substitution reaction proceeds with retention of the configuration at the asymmetric carbon atom in the first case, and with inversion of the configuration in the second case.

  4. 4.

    A hypothesis has been advanced concerning the causes of the different stereochemical courses of the electro Philic-substitution reactions in the cases investigated.

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Literature Cited

  1. E. Hughes, C. Ingold, C. Patel, J. Chem. Soc., 526 (1933); E. Hughes, C. Ingold, ibid. 1571 (1933); I. Gleave, E. Hughes, C. Ingold, ibid. 236 (1935); E. Hughes, C. Ingold, ibid. 244 (1935); 255 (1936); E Hughes, ibid. 255 (1935); E. Hughes, U. Shapiro, ibid, 1177 (1937); K. Cooper, E. Hughes. ibid. 1183 (1937); L, Bateman, E. Hughes, ibid. 1187 (1937), E. Hughes, U. Shapiro, ibid. 1192 (1937); L. Bateman, E. Hughes, G. Ingold, ibid. 881 (1938).

  2. C. Swain, J. Am. Chem. Soc. 10, 1119 (1948); 71, 2989 (1949).

    Google Scholar 

  3. A. N. Nesmeyanov, O. A. Reutov, and S. S. Poddubnaya, Bull. Acad. Sci. USSR. Div. Chem. Sci., No. 4, 649 (1953).

  4. H. Phillips, J. Kenyon et.al., J. Chem. Soc. 127, 2552 (1925); 2079 (1926); 188 (1927).

    Google Scholar 

  5. G. Woolett, V. Coulter, J. Am. Chem. Soc. 56, 1922 (1934).

    Google Scholar 

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Nesmeyanov, A.N., Reutov, O.A. & Poddubnaya, S.S. Optically active organomercury compounds Communication 2. Mechanism of electrophilic substitution at a saturated carbon atom. Russ Chem Bull 2, 753–760 (1953). https://doi.org/10.1007/BF01178853

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  • DOI: https://doi.org/10.1007/BF01178853

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