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Salt effects and the mechanism of electrophilic mercuration of unsaturated compounds

3. The reaction of mercury acetate with bornylene in the presence of sodium acetate in water-organic media

  • Organometallic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction of Hg(OAc)2 with bornylene in THF-H2O and CH3CN-H2O mixed solvents (75 ∶ 25, v/v) was studied. The effects of the addition of NaOAc on the reaction rate and the composition of products were investigated. In the CH3CN-H2O mixture, the addition of NaOAc decreases the amount of the rearranged product, fundamentally changes the ratio between the regioisomeric solvoadducts, and promotes the formation of products of Hg(OAc)2 addition. The reaction proceedsvia an ion pair and free mercurinium ion; the cation of the ion pair and the free mercurinium ion have dissimilar structures.

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Authors and Affiliations

  1. Nizhnii Novgorod Technical State University, 24 ul. Minina, 603600, Nizhnii Novgorod

    V. R. Kartashov, N. V. Malisova, A. B. Radbil, T. N. Sokolova & O. V. Vasiljeva

Authors
  1. V. R. Kartashov
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  2. N. V. Malisova
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  3. A. B. Radbil
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  4. T. N. Sokolova
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  5. O. V. Vasiljeva
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 544–548, March, 1995.

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Kartashov, V.R., Malisova, N.V., Radbil, A.B. et al. Salt effects and the mechanism of electrophilic mercuration of unsaturated compounds. Russ Chem Bull 44, 527–531 (1995). https://doi.org/10.1007/BF00702403

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  • DOI: https://doi.org/10.1007/BF00702403

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