Summary
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1.
Two diastereoisomers of the di-(-)-menthyl ester of mercuribis[phenylacetic acid] have been prepared in the pure state.
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2.
The mechanism of the symmetrization of organomercury compounds of the aliphatic series under the action of nucleophilic reagents has been elucidated.
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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.
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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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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