Nucleophilic substitution reactions of allylic halides carrying electron-withdrawing substituents in the γ-position. Formation of cyclopropanes from dimethyl 2-bromo-2-methylpropylidenemalonate
Abstract
Reaction of dimethyl 2-bromo-2-methylpropylidenemalonate with sodium methoxide or potassium cyanide in methanol produces cyclopropane derivatives in high yields, thus indicating an overall substitution with nucleophilic attack occurring at the β-position of the allylic halide.