ISSN:
1573-9171
Keywords:
mercury acetate
;
bornylene
;
ion pair
;
mercurinium ion
;
solvomercuration
;
salt effect
;
regioisomers
;
reaction mechanism
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00702403
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