The anti-Markownikoff products of bromination and bromomethoxylation of 3-methylenecyclo-butane-1-carbonitrile and methyl 3-methylenecyclobutane-1-carboxylate were subjected to dehydrobromination by the action of potassium tert-butoxide in THE The reaction takes two elimination pathways: 1,3-de-hydrobromination to give bicyclobutane derivatives and 1,2-dehydrobromination leading to substituted methylenecyclobutane. Structural factors in the substrate were revealed, which are responsible for the ratio of the two concurrent elimination processes.
The anti-Markownikoff products of bromination and bromomethoxylation of 3-methylenecyclo-butane-1-carbonitrile and methyl 3-methylenecyclobutane-1-carboxylate were subjected to dehydrobromination by the action of potassium tert-butoxide in THE The reaction takes two elimination pathways: 1,3-de-hydrobromination to give bicyclobutane derivatives and 1,2-dehydrobromination leading to substituted methylenecyclobutane. Structural factors in the substrate were revealed, which are responsible for the ratio of the two concurrent elimination processes.