'Conjugate' Substitution of Hydrogen in the Methyl Group of Pentabromotoluene in the Presence of Strong Bases

摘要

The reactions of pentabromotoluene with i-PrONa or t-BuONa in pyridine give N-(pentabromo-benzyl)pyridinium bromide and a mixture of isomeric tetrabromotoluenes.In the presence of bromine or carbon tetrabromide,the reductive debromination is blocked,and the reactions involve exclusively substitution of hydrogen in the methyl group of pentabromotoluene by the pyridinium residue.