Abstract
Apart from the common bromine-lithium exchange reaction in brominated aromatic compounds, it is possible to obtain a lithio-derivative quite different from the one usually described in such a reaction. This new reaction, which results from a special experimental conditions is called ·homotransmetalation”, and it occurs when using n-butyllithium and 3-bromo 2-halogenopyridines ( 1). Different behaviour is observed with the three similar compounds ( 1: X = F,Cl,Br). Explanations are proposed of these results. It is then possible to compare the relative stabilities of the proposed lithio-structures. It is evident that nucleophilic substitution of bromine in position 4 of the pyridine ring is easier than is usually recognised.
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