25273-25-0Relevant articles and documents
ALKOXYLATION DURING THE DEHALOGENATION OF 2,3-DIBROMOBICYCLOHEPTANE WITH ZINC DUST IN ALCOHOL SOLUTION
Gasanov, A. G.,Nagiev, A. V.,Alieva, L. I.
, p. 835 - 836 (2007/10/03)
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Solvomercuration-Demercuration. 11. Alkoxymercuration-Demercuration of Representative Alkenes in Alcohol Solvents with the Mercuric Salts Acetate, Trifluoroacetate, Nitrate, and Methanesulfonate
Brown, Herbert C.,Kurek, Joseph T.,Rei, Min-Hon,Thompson, Kerry L.
, p. 2551 - 2557 (2007/10/02)
The alkoxymercuration-demercuration of seven representative olefins with the mercuric salts acetate, trifluoroacetate, nitrate, and methanesulfonate, in methyl, ethyl, isopropyl, and tert-butyl alcohols was examined.Mercuric acetate was effective only in methanol and ethanol.On the other hand, mercuric trifluoroacetate was effective in all four solvents, giving in most cases high yields of the corresponding ethers.Both mercuric nitrate and mercuric methanesulfonate were effective in methanol, ethanol, and 2-propanol.However, in several cases poor selectivity for the ether was observed, as evidenced by the formation of significant amounts of side products.Both electronic and steric effects are important factors in the reaction.Moreover, the structure of the olefin has a pronounced effect, both on the types of oxymercurials formed and on their stability to the reaction conditions.
Hindered Nucleophilic Displacement (SN2) Reactions of 2exo- and 2endo-Norbornyl Derivatives. Norbornane Series 4.
Grob, Cyril A.,Lutz, Erich
, p. 153 - 160 (2007/10/02)
The reactions of 2exo- and 2endo-norbornyl bromide (1 e and 2 e, respectively) in 90 percent ethanol with a large excess of potassium hydroxide, and 2exo-norbornyl-p-toluenesulfonate (1 g) with excess sodium thiophenolate in methyl cellosolve, have been studied.They obey the first order rate law and are zero order with respect to the base-nucleophile.However, the ratio of 1,2- and 1,3-elimination to exo-substitution products depends strongly on the base-nucleophile concentration.The extreme inertness of 2-norbornyl derivatives in displacement reactions is due to severe steric hindrance of rearside nucleophilic attack, a feature they have in common with other bi- and tricyclic molecules bearing nucleofugal groups adjacent to one or two bridgehead atoms.