Salt effects in the mercuration of unsaturated compounds. Kinetic evidence for the formation of ion pairs and a solvated ion |
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| Authors: | V. R. Kartashov T. N. Sokolova I. V. Timofeev E. V. Skorobogatova N. S. Zefirov |
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| Affiliation: | (1) Nizhnii Novgorod State Technical University, 24 ul. K. Minina, 603600 Nizhnii Novgorod, Russian Federation;(2) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899 Moscow, Russian Federation |
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| Abstract: | The kinetics of mercuration of bornylene and cyclohexene in different solvents in the presence of NaOAc and LiClO4 has been investigated. Addition of NaOAc sharply decreases the rate of addition reactions of mercuric acetate to bornylene and cyclohexene in alcohols; the main direction of the mercuration of bornylene is the formation of acetoxy-adducts, and the yield of solvo-adducts decreases from 76 % in the absence of NaOAc, to 19 % in the presence of the salt (4·10–3 mol L–1). A reaction scheme involving the participation of intermediate ion pairs and a solvated mercurinium ion is suggested and confirmed by a steady-state concentration method. The influence of NaOAc on the rate of the reaction and on product formation is realized through the common ion effect.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 819–826, May, 1994. |
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| Keywords: | bornylene, mercuration, kinetics salt effect common ion effect ion pair, solvated ion reaction mechanism |
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