ISSN:
1573-9171
Keywords:
bornylene, mercuration, kinetics
;
salt effect
;
common ion effect
;
ion pair, solvated ion
;
reaction mechanism
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00717334
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