Abstract
The structures of the products of the reaction of arylphenyl-substituted alkynes with mercury acetate in methanol and acetic acid as well as the stereo- and regiochemistry of the reaction were determined. The reaction in methanol has an unusual regiochemistry,viz., the electrophilic fragment of Hg(OAc)2 adds to the carbon atom bearing the aryl substituent. The reaction in acetic acid yieldstrans-products. The kinetics of these reactions were investigated, and a correlation analysis of the kinetic data was carried out. For the reaction in CH3OH, the effects of the addition of NaOAc on the reaction rate and on the ratio between the products were determined. Mechanisms for the reactions were suggested and discussed.
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For Parts 1–3, see Refs 1–3.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 549–553, March, 1995.
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Kartashov, V.R., Sokolova, T.N., Leksina, O.A. et al. Salt effects and the mechanism of electrophilic mercuration of unsaturated compounds. Russ Chem Bull 44, 532–536 (1995). https://doi.org/10.1007/BF00702404
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DOI: https://doi.org/10.1007/BF00702404