Reaction of diethyl dibromomalonate with methoxide: Evidence for a novel bromophilic attack
Reaction of diethyl dibromomalonate (1) with sodium methoxide in cyclohexene yields dibromonorcarane (2) as the major product. This product forms via the capture of dibromocarbene (4) by cyclohexene. Dibromocarbene, in turn, is generated from ethyl tribromoacetate (6) which evidence suggests arises via a bromophilic attack between the carboethoxydibromomethyl carbanion (7) and diethyldibromomalonate (1).
Mebane, Robert C.,Smith, Keegan M.,Rucker, Darlene R.,Foster, Michael P.
gem-Dihalocyclopropane formation by iron/copper activation of tetrahalomethanes in the presence of nucleophilic olefins. Evidence for a carbene pathway
The activation of CBr4 and CCl4 by a bimetallic iron/copper couple in acetonitrile is a new, inexpensive, nontoxic and efficient procedure for gem-dibromo- and gem-dichloromethylenation of nucleophilic alkenes. This new route to gem-dihalocyclopropanes involves dihalocarbene species.
Léonel, Eric,Lejaye, Michael,Oudeyer, Sylvain,Paugam, Jean Paul,Nédélec, Jean-Yves
p. 2635 - 2638
(2007/10/03)
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